Compound characterization data — Momm et al., 2026

Sarah N. Momm, Beatrice Massone, Maria Lillevang Madsen, Luca Laraia. “Bifunctional, steroidal photoaffinity probes enable targeting of sterol transport proteins.” ChemRxiv (2026). https://doi.org/10.26434/chemrxiv.15007958/v1

Methyl (4R)-4-[(3R,6S,8S,9S,10R,13R,14S,17R)-3,6-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-3
¹H NMR (400 MHz, CDCl₃)	δ = 0.66 (s, 3H, C18-H3)ⁱⁱ, 0.92 (s, 3H, C19-H3)ⁱⁱ superimposed by 0.93 (d, J4′,5′ = 6.1 Hz, 3H, C5′-H3)ⁱⁱ, 1.02 – 1.23 (m, 6H, C1-H2, C2-H2, C4-H2)ⁱ, 1.25 – 1.50 (m, 8H, C5-H, C7-H2, C8-H, C9-H, C11-H2, C14-H)ⁱ, 1.56 – 2.01 (m, 12H, C12-H2, C15-H2, C16-H2, C17-H, C4-H, C3′-H2, C3-OH, C6-OH)ⁱ, AB signal (δA = 2.37, δB = 2.24, ²JAB = 15.7 Hz, additional splitting A: dd, JA,3′A = 10.3 Hz, JA,3′B = 5.3 Hz, additional splitting B: dd, JB,3′A = 6.7 Hz, JB,3′B = 9.7 Hz, 2H, C2′-H2), 3.64 (mc, 1H, C3-H)ⁱ, 3.68 (s, 3H, C1′-OCH3), 4.07 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

Methyl (4R)-4-[(3R,6S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3,6-bis(tosyloxy)hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-4
¹H NMR (400 MHz, CDCl₃, contains traces of impurities at δ = 7.52, 7.94 and 8.69 ppm)	δ = 0.58 (s, 3H, C18-H3), 0.80 (s, 3H, C19-H3), 0.87 (d, J4′,5′ = 6.0 Hz, 3H, C5′-H3), 0.90 – 1.18 (m, 7H, C1-H2, C2-H2, C4-H2, C5-H)ⁱ, 1.21 – 1.40 (m, 6H, C7-CH2, C8-H, C9-H, C11-H2)ⁱ, 1.42 – 1.53 (m, 3H, C12-H2, C14-H)ⁱ, 1.57 – 1.66 (m, 2H, C15-H2)ⁱ, 1.68 – 1.96 (m, 6H, C16-H2, C17-H, C4′-H, C3′-H2)ⁱ, AB signal (δA = 2.33, δB = 2.21, JAB = 15.1 Hz, additional splitting A: J3′A,A = 10.0 Hz, J3′B,A = 5.5 Hz; additional splitting B: J3′A,B = 7.0 Hz, J3′B,B = 9.6 Hz, 2H, 2′-CH2), 2.46 (s, 6H, 2 × C4″-H3), 3.66 (s, 3H, C1′-OCH3), 4.30 (mc, 1H, C3-H)ⁱⁱ, 4.78 (ddd, J5,6 = 12.1 Hz, J7A,6 = 4.7 Hz, J7B,6 = 4.7 Hz, 1H, C6-H), 7.34 (mc, 4H, 2 × C2″-H, C6″-H)ⁱ, 7.75 (mc, 4H, 2 × C3″-H, C5″-H)ⁱ ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

Methyl (R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-5
¹H NMR (400 MHz, CDCl₃)	δ = 0.68 (s, 3H, C18-H3)ⁱⁱ, 0.92 (d, J4′,5′ = 6.1 Hz, 3H, C5′-H3) superimposed by (m, 1H, C9-H)ⁱⁱ, 1.00 (s, 3H, C19-H3) superimposed by (m, 1H, C1-HA)ⁱⁱ, 1.03 – 1.20 (m, 4H, C2-H2, C3′-H2)ⁱ, 1.24 – 1.36 (m, 2H, C1-HB, C8-H)ⁱ, 1.31 – 1.61 (m, 8H, C7-H2, C11-H2, C12-H2, C15-H2)ⁱ, 1.74 – 1.90 (m, 4H, C16-H2, C17-H, C4′-H), 1.92 – 2.03 (m, 2H, C14-H, C3-OH)ⁱ, 2.16 – 2.30 (m, 3H, C4-H2, C2′-HB)ⁱⁱ, 2.35 (ddd, J2′A,2′B = 15.4 Hz, J3′A,2′B = 10.1 Hz, J3′B,2′B = 5.3 Hz, 1H, C2′-HA)ⁱⁱ, 3.51 (mc, 1H, C3-H), 3.66 (s, 3H, 1′-OCH3), 5.34 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Identifier	Steroidal building block A, 6
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C18-H3)ⁱⁱ, 0.89 [s, 9H, C3-OSiC(CH3)3], 0.94 (d, J4′,5′ = 6.3 Hz, 3H, C5′-H3)ⁱⁱ superimposed by (m, 1H, C9-H)ⁱⁱ, 1.00 (s, 3H, C19-H3), 1.02 – 1.20 (m, 4H, C1-H2, C2-H2)ⁱ, 1.24 – 1.39 (m, 3H, C7-H2, C8-H)ⁱ, 1.40 – 1.64 (m, 7H, C11-H2, C12-H2, C14-H, C15-H2)ⁱ, 1.67 – 1.75 (m, 1H, C17-H)ⁱ, 1.76 – 1.92 (m, 3H, C16-H2, C4′-H)ⁱ, 1.92 – 2.03 (m, 2H, C3′-H2)ⁱ, 2.16 (ddd, ²J4B,4A = 13.1 Hz, J3,4A = 5.1 Hz, ⁴J6,4A = 2.3 Hz, 1H, C4-HA)ⁱⁱ, 2.21 – 2.31 (m, 2H, C4-HB, C2′-HA)ⁱⁱ, 2.40 (ddd, ²J2′A,2′B = 15.4 Hz, J3′A,2′B = 10.2 Hz, J3′B,2′B = 5.2 Hz, 1H, C2′-HB)ⁱⁱ, 3.48 (mc, 1H, C3-H), 5.32 (mc, 1H, C6-H), 9.99 (br. s, 1H, 1′-COOH) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

(3S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
Identifier	SI-7
¹H NMR (400 MHz, DMSO-d₆, the solvent contains H₂O with a signal at δ = 3.31 ppm)	δ = 0.63 (s, 3H, C18-H3)ⁱⁱ, 0.94 (s, 3H, C19-H3)ⁱⁱ superimposed by (m, 2H, C9-H, C8-H)ⁱ, 1.02 – 1.11 (m, 1H, C1-HA)ⁱ, 1.12 – 1.27 (m, 2H, C1-HB, C2-HA)ⁱ, 1.28 – 1.45 (m, 3H, C2-HB, C4-H2)ⁱ, 1.47 – 1.58 (m, 2H, C7-H2)ⁱ, 1.58 – 1.72 (m, 3H, C11-H2, C12-HA)ⁱ, 1.76 (mc, 1H, C12-HB)ⁱ, 1.87 – 2.01 (m, 3H, C14-H, C15-H2)ⁱ, 2.03 – 2.18 (m, 2H, C16-H2)ⁱ, 2.26 (dd, J16A,17 = 9.2 Hz, J16B,17 = 9.2 Hz, 1H, C17-H), 3.25 (mc, 1H, C3-H), 4.49 (br. s, 1H, C3-OH), 5.26 (mc, 1H, C6-H), 11.88 (s, 1H, 17-COOH) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

(3S,9S,10R,13S,14S,17S)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
Identifier	Steroidal building block B, 7
Specific rotation	[αD] = −12.4 (c = 0.854, CHCl₃)
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.74 (s, 3H, C18-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.90 – 0.98 (m, 1H, C9-H), 1.00 (s, 3H, C19-H3), 1.03 – 1.16 (m, 2H, C14-H, C1-HA), 1.22 – 1.33 (m, 2H, C15-HA, C12-HA), 1.41 – 1.62 (m, 5H, C7-HA, C2-HA, C11-H2, C8-H), 1.66 – 1.76 (m, 2H, C2-HB, C15-HB), 1.77 – 1.88 (m, 2H, C1-HB, C16-HA), 1.96 – 2.04 (m, 1H, C7-HA), 2.05 – 2.14 (m, 2H, C16-HB, C12-HB), 2.17 (mc, 1H, C4-HA), 2.27 (mc, 1H, C4-HB), 2.39 (dd, J16A,17 = 9.5 Hz, J16B,17 = 9.5 Hz, 1H, C17-H), 3.51 (mc, 1H, C3-H), 5.33 (mc, 1H, C6-H), 9.59 [br. s, 1H, 17-C(O)OH] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.58 [C3-OSi(CH3)2], 13.17 (C-18), 18.27 [C3-OSiC(CH3)3], 19.45 (C-19), 20.90 (C-11), 23.48 (C-16), 24.57 (C-15), 25.95 [C3-OSiC(CH3)3], 31.86 (C-7), 32.05 (C-8, C-2), 36.66 (C-10), 37.40 (C-1), 38.04 (C-12), 42.79 (C-4), 44.13 (C-13), 50.13 (C-9), 54.97 (C-17), 56.33 (C-14), 72.57 (C-3), 120.81 (C-6), 141.67 (C-5), 178.99 [17-C(O)OH] ppm
IR ṽ (cm⁻¹)	2958 (s), 2930 (s), 2897 (s), 2856 (s), 1731 (m), 1704 (s), 1471 (m), 1460 (m), 1436 (m), 1383 (m), 1361 (m), 1293 (w), 1255 (m), 1194 (w), 1132 (w), 1086 (s), 1005 (w), 958 (w), 939 (w), 887 (m), 870 (m), 837 (m), 803 (w), 771 (m)

1-[(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethan-1-one
Identifier	SI-8
¹H NMR (400 MHz, CDCl₃)	δ = 0.60 (s, 3H, C18-H3)ⁱⁱ, 0.68 (mc, 1H, C9-H)ⁱⁱ, 0.80 (s, 3H, C19-H3)ⁱⁱ, 0.86 – 1.03 (m, 2H, C1-H2)ⁱ, 1.06 – 1.23 (m, 3H, C2-H2, C4-HA)ⁱ, 1.23 – 1.34 (m, 4H, C4-HB, C6-H2, C7-HA)ⁱ, 1.34 – 1.44 (m, 3H, C7-HB, C8-H, C11-HA)ⁱ, 1.53 – 1.75 (m, 6H, C5-H, C11-HB, C12-H2, C14-H, C15-HA)ⁱ, 1.77 – 1.84 (m, 1H, C15-HB)ⁱ, 1.97 – 2.02 (m, 1H, C16-HA)ⁱ, 2.06 – 2.19 (m, 1H, C16-HB)ⁱ superimposed by 2.10 (s, 3H, C2′-H3)ⁱⁱ, 2.50 (t, ³J17,16 = 9.0 Hz, C17-H)ⁱⁱ, 3.60 (mc, 1H, C3-H)ⁱⁱ ppm
Additional ¹H NMR (400 MHz, DMSO-d₆)	δ = 4.49 (3-OH)ⁱⁱ ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following protons is interchangeable: C1-H2, C2-H2, C4-H2, C5-H, C6-H2, C7-H2, C8-H, C11-H2, C12-H2, C14-H, C15-H2, C16-H2
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of similar structures. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

(3S,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
Identifier	SI-9
¹H NMR (400 MHz, CDCl₃)	δ = 0.63 – 0.70 (m, 1H, C9-H)ⁱ, 0.72 (s, 3H, C18-H3)ⁱ, 0.81 (s, 3H, C19-H3)ⁱ, 0.85 – 1.03 (m, 2H, C1-H2)ⁱⁱ, 1.05 – 1.15 (m, 2H, C2-H2)ⁱⁱ, 1.18 – 1.46 (m, 8H, C4-H2, C5-H, C6-H2, C7-H2, C8-H)ⁱ, 1.51 – 1.60 (m, 2H, C11-H2)ⁱⁱ, 1.64 – 1.76 (m, 3H, C14-H, C12-H2)ⁱⁱ, 1.76 – 1.85 (m, 2H, C15-H2)ⁱⁱ, 2.00 – 2.12 (m, 2H, C16-H2)ⁱⁱ, 2.37 (t, J16,17 = 9.3 Hz, 1H, C17-H)ⁱ, 3.60 (mc, 1H, C3-H) ppm
¹H NMR assignment qualifier i	The assignment of this signal was possible through comparison with the NMR analysis of similar structures. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹H NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following protons is interchangeable: C1-H2, C2-H2, C4-H2, C5-H, C6-H2, C7-H2, C8-H, C11-H2, C12-H2, C14-H, C15-H2, C16-H2

(5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylic acid
Identifier	Steroidal building block C, 8
¹H NMR (400 MHz, CDCl₃)	δ = 0.75 (s, 3H, C18-H3)ⁱⁱ, 0.76 – 0.82 (m, 1H, C9-H)ⁱⁱ, 0.82 – 0.92 (m, 1H, C8-H)ⁱ, 0.92 – 0.98 (m, 1H, C1-HA)ⁱ, 1.02 (s, 3H, C10-H3)ⁱⁱ, 1.08 – 1.18 (m, 1H, C14-H)ⁱⁱ, 1.20 – 1.43 (m, 6H, C1-HB, C2-H2, C4-H2, C5-H)ⁱⁱ, 1.44 – 1.62 (m, 2H, C6-H2)ⁱⁱ, 1.66 – 1.76 (m, 2H, C7-H2)ⁱⁱ, 1.76 – 1.88 (m, 1H, C11-HA)ⁱⁱ, 2.06 – 2.14 (m, 4H, C11-HB, C12-H2, C15-HA)ⁱ, 2.21 – 2.45 (m, 4H, C15-HB, C16-H2, C17-Hⁱⁱ)ⁱ ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following protons is interchangeable: C1-H2, C2-H2, C4-H2, C5-H, C6-H2, C7-H2, C8-H, C11-H2, C12-H2, C15-H2, C16-H2
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of similar structures. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis

Ethyl 3-oxohept-6-ynoate
Identifier	SI-11
¹H NMR (400 MHz, CDCl₃, keto-tautomer)	δ = 1.26 (mc, 3H, C2′-H3), 1.94 (mc, 1H, C7-H), 2.45 (mc, 2H, 4C-H2), 2.79 (mc, 2H, C5-H2), 3.43 – 3.46 (m, 2H, C2-H2), 4.18 (mc, 2H, C1′-H2) ppm
¹H NMR (400 MHz, CDCl₃, enol-tautomer)	δ = 1.23 (mc, 3H, C2′-H3), 2.00 – 2.02 (m, 1H, C7-H), 2.24 – 2.26 (m, 2H, C4-H2), 2.37 – 2.42 (m, 2H, C5-H2), 4.09 (mc, 2H, C1′-H2), 5.03 (m, 1H, C2-H), 12.08 (mc, 1H, C3-OH) ppm

Ethyl 2-[2-(but-3-yn-1-yl)-1,3-dioxolan-2-yl]acetate
Identifier	SI-12
¹H NMR (400 MHz, CDCl₃)	δ = 1.26 (t, J2′,1′ = 7.2 Hz, 2H, C1′-H2), 1.93 (t, ⁴J5,7 = 2.7 Hz, 1H, C7-H), 2.12 (mc, 2H, C5-H2)ⁱ, 2.31 (mc, 2H, C4-H2)ⁱ, 2.65 (s, 2H, C2-H2), 3.98 (mc, 4H, C1″-H2, C2″-H2), 4.15 (q, J1′,2′ = 7.3 Hz, 2H, C2′-H2) ppm

2-[2-(But-3-yn-1-yl)-1,3-dioxolan-2-yl]ethan-1-ol
Identifier	SI-13
¹H NMR (400 MHz, CDCl₃)	δ = 1.90 – 1.96 (m, 5H, C2-H2, C4-H2, C7-H), 2.27 (mc, 2H, C5-H2), 2.34 (br. s, 1H, C1-OH), 3.75 (dd, J2A,1 = 5.6 Hz, J2B,1 = 5.6 Hz, 2H, C1-H2), 4.00 (mc, 4H, C1′-H2, C2′-H2) ppm

1-Hydroxyhept-6-yn-3-one
Identifier	SI-14
¹H NMR (400 MHz, CDCl₃)	δ = 1.95 (t, J5,7 = 2.7 Hz, 1H, C7-H), 2.16 – 2.26 (br. m, 1H, C1-OH), 2.56 (td, J4,5 = 7.5 Hz, ⁴J7,5 = 2.7 Hz, 2H, C5-H2), 2.62 – 2.72 (m, 4H, C2-H2, C4-H2), 3.86 (mc, 2H, C1-H2) ppm

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethan-1-ol
Identifier	Diazirine A, 9
¹H NMR (400 MHz, CDCl₃)	δ = 1.65 – 1.73 (m, 4H, C2-H2, C4-H2), 1.91 (br. s, 1H, C1-OH), 1.98 – 2.09 (m, 3H, C7-H, C5-H2), 3.49 (t, J2,1 = 6.2 Hz, 2H, C1-H2) ppm

Methyl 3-oxohept-6-ynoate
Identifier	SI-16
¹H NMR (400 MHz, CDCl₃, keto-tautomer)	δ = 1.96 (t, ⁴J5,7 = 2.7 Hz, 1H, C7-H), 2.47 (td, J4,5 = 7.4 Hz, ⁴J7,5 = 2.7 Hz, 2H, C5-H2), 2.81 (t, J5,4 = 7.0 Hz, 2H, C4-H2), 3.48 (mc, 2H, C2-H2), 3.74 (s, 3H, C1-OCH3) ppm

3-Oxohept-6-ynoic acid
Identifier	SI-17
¹H NMR (400 MHz, CDCl₃, keto-tautomer)	δ = 1.98 (t, J5,7 = 2.7 Hz, 1H, C7-H), 2.50 (td, J4,5 = 7.4 Hz, ⁴J7,5 = 2.7 Hz, 2H, C5-H2), 2.84 (t, J5,4 = 6.8 Hz, 2H, C4-H2), 3.55 (mc, 2H, C2-H2), 9.33 (br. s, 1H, C1-OH) ppm
¹H NMR (400 MHz, CDCl₃, enol-tautomer)	δ = 2.01 (t, J5,7 = 2.3 Hz, 1H, C7-H), 2.45 – 2.53 (m superimposed by td from keto-tautomer, 4H, C5-H2, C4-H2), 5.11 (s, 1H, C2-H), 9.33 [br. s, 1H, C1-OH], 11.76 (s, 1H, C3-OH) ppm

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]acetic acid
Identifier	Diazirine B, 10
¹H NMR (400 MHz, CDCl₃, crude product, the sample contains EtOAc with signals at δ = 1.26, 2.04, 4.12 ppm and CH₂Cl₂ with a signal at δ = 5.31 ppm as well as some impurities at δ = 2.35 – 2.73 ppm)	δ = 1.83 (t, J5,4 = 7.3 Hz, 2H, C4-H2), 2.03 (t, ⁴J5,7 = 2.5 Hz, 1H, C7-H), 2.09 (td, J4,5 = 7.5 Hz, ⁴J7,5 = 2.1 Hz, 2H, C5-H2), 2.42 (s, 2H, C2-H2), 8.94 (br. s, 1H, C1-OH) ppm

2-(3-Methyl-3H-diazirin-3-yl)ethan-1-ol
Identifier	SI-19
¹H NMR (400 MHz, CDCl₃, the spectrum contains 25 wt-% of Et₂O with signals at δ = 1.20 (t), 3.47 (q) ppm)	δ = 1.07 (s, 3H, C4-H3), 1.57 (br. s, 1H, C1-OH), 1.64 (t, J1,2 = 6.2 Hz, 2H, C2-H2), 3.56 (t, J2,1 = 6.3 Hz, 2H, C1-H2) ppm

2-(3-Methyl-3H-diazirin-3-yl)ethyl 4-methylbenzenesulfonate
Identifier	SI-20
¹H NMR (400 MHz, CDCl₃, the spectrum contains traces of CH₂Cl₂ with a signal at δ = 5.31 ppm)	δ = 1.00 (s, 3H, C4-H3), 1.67 (t, J1,2 = 6.2 Hz, 2H, C2-H2), 2.45 (s, 3H, C4′-H3), 3.95 (t, J2,1 = 6.4 Hz, 2H, C1-H2), 7.36 (mc, 2H, C3′-H, C5′-H)ⁱ, 7.81 (mc, 2H, C2′-H, C6′-H)ⁱ ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable

N-[2-(3-Methyl-3H-diazirin-3-yl)ethyl]-4-nitro-N-(prop-2-yn-1-yl)benzenesulfonamide
Identifier	SI-22
¹H NMR (400 MHz, CDCl₃, the spectrum contains traces of EtOAc with signals at δ = 1.26, 2.04, 4.12 ppm)	δ = 1.09 (s, 3H, C4-H3), 1.64 (dd, J1A,2 = 7.7 Hz, J1B,2 = 7.7 Hz, 2H, C2-H2), 2.04 (dd, ⁴J1″A,3″ = 2.6 Hz, ⁴J1″B,3″ = 2.6 Hz, 1H, C3″-H), 3.21 (dd, J2A,1 = 7.4 Hz, J2B,1 = 7.4 Hz, 2H, C1-H2), 4.19 (d, ⁴J3″,1″ = 2.6 Hz, 2H. C1″-H2), 8.05 (mc, 2H, C3′-H, C5′-H)ⁱ, 8.37 (mc, 2H, C2′-H, C6′-H)ⁱ ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable

N-[2-(3-methyl-3H-diazirin-3-yl)ethyl]prop-2-yn-1-amine hydrochloride
Identifier	Diazirine C, 11
¹H NMR (400 MHz, DMSO-d₆)	δ = 1.05 (s, 3H, C4-H3), 1.72 (mc, 2H, C2-H2), 2.91 (mc, 2H, C1-H2), 3.72 (t, ⁴J1′,3′ = 2.7 Hz, 1H, C3′-H), 3.87 (d, ⁴J3′,1′ = 2.6 Hz, 2H, C1′-H2), 9.60 (br. s, 1H, C1-NH) ppm

(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanamide
Identifier	SI-23
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C18-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.89 – 0.93 (m, 1H, C9-H), 0.94 (d, J4′,5′ = 6.7 Hz, 3H, C5′-H3), 0.99 (s, 3H, C19-H3) superimposed by (m, 1H, C14-H), 1.01 – 1.20 (m, 4H, C17-H, C16-HA, C12-HA, C1-HA), 1.25 – 1.38 (m, 2H, C3′-HA, C15-HA), 1.40 – 1.64 (m, 7H, c4′-H, C16-HB, C8-H, C7-HA, C2-HA, C11-H2)ⁱ, 1.67 – 1.75 (m, 1H, C2-HB), 1.75 – 1.92 (m, 3H, C3′-HB, C15-HB, C1-HB), 1.92 – 2.03 (m, 2H, C12-HB, C7-HB), 2.07 – 2.20 (m, 2H, C4-HA, C2′-HA), 2.22 – 2.33 (m, 2H, C4-HB, C2′-HB), 3.48 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H) superimposed by (br. m, 2H, C1′-NH2) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹³C NMR (100 MHz, CDCl₃)	δ = −4.58 [C3-OSi(CH3)2], 11.88 (C-18), 18.28 [C3-OSiC(CH3)3], 18.42 (5′-CH3), 19.43 (C-19), 21.06 (C-11)ⁱⁱ, 24.26 (C-16), 25.95 [C3-OSiC(CH3)3], 28.20 (C-15), 31.64 (C-3′), 31.91 (C-7, C-8), 32.09 (C-2), 32.80 (C-2′), 35.48 (C-4′), 36.59 (C-10), 37.39 (C-1), 39.79 (C-12), 42.40 (C-13), 42.82 (C-4), 50.17 (C-9), 55.80 (C-17), 56.78 (C-14), 72.64 (C-3), 121.12 (C-6), 141.57 (C-5), 175.89 (C-1′) ppm
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −27.1 (c = 0.515, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₃₀H₅₄NO₂Si [M+H]⁺: 488.3924; found: 488.3924 (Δ = 0.03 ppm)
IR ṽ	3311 (br), 2936 (s), 2903 (s), 2867 (s), 2341 (w), 1733 (m, br), 1680 (m, br), 1636 (m, br), 1584 (m, br), 1436 (m), 1379 (m), 1250 (m), 1206 (m), 1179 (m), 1134 (m), 1110 (m), 1096 (m), 1058 (m), 959 (w), 888 (w), 871 (w), 838 (w), 804 (m), 775 (m) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]-N-{(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl}acetamide
Identifier	SI-24
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.67 (s, 3H, C18-H3), 0.89 [s, 9H, C3-OSiC(CH3)3] superimposed by (m, 1H, C9-H), 0.93 (d, J4′,5′ = 6.6 Hz, 3H, C5′-H3), 1.08 (s, 3H, C19-H3) superimposed by 0.95 – 1.01 (m, 1H, C14-H), 1.02 – 1.17 (m, 5H, C3′-HA, C17-H, 15-HA, C1-HA, C12-HA), 1.20 – 1.30 (m, 1H, C16-HA), 1.37 – 1.65 (m, 9H, C3′-HB, C4′-H, C15-HB, C8-H, C2-HA, C11-H2, C2′-H2)ⁱ, 1.67 – 1.73 (m, 1H, C2-HB), 1.77 (t, J5″,4″ = 7.3 Hz, 2H, C4″-H2) superimposed by 1.73 – 1.87 (m, 3H, C16-HB, C7-HA, C1-HA), 1.92 – 2.02 (m, 2H, C7-HB, C12-HB) superimposed by 2.01 (t, J5″,7″ = 2.7 Hz, 1H, C7″-H), 2.04 – 2.11 (m, 2H, C5″-H3), 2.16 (mc, 1H, C4-HA), 2.21 – 2.31 (m, 1H, C4-HA) superimposed by 2.23 (s, 2H, C2″-H2), 3.23 (mc, 2H, C1′-H2), 3.48 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H), 5.72 (br. m, 1H, C1′-NH) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁵N NMR (41 MHz, CDCl₃)	δ = 56.01 (C3′-N=N), 119.35 [C1″-NH] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.58 [C3-OSi(CH3)2], 11.86 (C-18), 13.30 (C-5″), 18.27 [C3-OSiC(CH3)3], 18.67 (C-5′), 19.43 (C-19), 21.06 (C-11), 24.27 (C-15), 25.95 [3-OSiC(CH3)3], 26.01 (C-3″), 26.14 (C-4″), 28.25 (C-16), 31.90 (C-1′)ⁱⁱ, 31.92 (C-8)ⁱⁱ, 31.94 (C-7)ⁱⁱ, 32.09 (C-2), 33.07 (C-3′), 35.46 (C-4′), 36.59 (C-10), 37.39 (C-1), 39.79 (C-12), 40.26 (C-1′), 41.70 (C-2″), 42.36 (C-13), 42.82 (C-4), 50.18 (C-9), 55.91 (C-17), 56.79 (C-14), 69.50 (C-7″), 72.64 (C-3), 82.64 (C-6″), 121.12 (C-6), 141.58 (C-5), 167.40 (C-1″) ppm
¹³C NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-8 / C-7 / C-4″
Specific rotation	[αD] = −18.5 (c = 0.630, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₃₇H₆₂N₃O₂Si [M+H]⁺: 608.4606; found: 608.4550
IR ṽ	3293 (m, br), 2928 (s), 2904 (s), 2881 (s), 2857 (s), 1763 (w), 1640 (s), 1555 (m, br), 1471 (m), 1459 (m), 1436 (m), 1382 (m), 1367 (m), 1341 (w), 1252 (m), 1222 (w), 1196 (w), 1134 (w), 1082 (s), 1025 (w), 1006 (w), 991 (w), 958 (w), 937 (w), 886 (m), 869 (m), 838 (m), 802 (w), 774 (m), 731 (w), 670 (w), 632 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]-N-[(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl]acetamide
Identifier	SPAP V, 17
¹H NMR (400 MHz, CDCl₃)	δ = 0.68 (s, 3H, C18-H3), 0.93 (d, J4,5 = 7.6 Hz, 3H, C5′-H3) superimposed by 0.87 – 0.96 (m, 1H, C9-H), 1.00 (s, 3H, C19-H3) superimposed by 0.96 – 1.03 (m, 1H, C14-H), 1.03 – 1.16 (m, 5H, C2-HA, C1-HA, C12-HA, C17-H, C3′-HA), 1.21 – 1.27 (m, 3H, C15-HA, C16-H2), 1.41 – 1.57 (m, 8H, C2-HB, C11-H2, C8-H, C4′-H, C3′-HB, C2′-H2), 1.77 (t, J5″,4″ = 7.6 Hz, 2H, C4″-H2), 1.80 – 1.88 (m, 3H, C1-HB, C7-HA, C15-HB), 1.92 – 1.99 (m, 2H, C7-HB, C12-HB), 2.00 (t, J5″,7″ = 2.7 Hz, 1H, C7″-H), 2.07 (mc, 2H, C5″-H2), 2.23 (s, 2H, C2″-H2), 2.23 – 2.32 (m, 2H, C4-H2), 3.22 (mc, 2H, C1′-H2), 3.52 (mc, 1H, C3-H), 5.35 (mc, 1H, C6-H), 5.72 (mc, 1H, C1′-NH) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 56.01 (C3″-N=N), 119.35 [C1″-NH] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.87 (C-18), 13.30 (C-5″), 18.66 (C-5′), 19.40 (C-19), 21.07 (C-11), 24.26 (C-2)ⁱ, 26.01 (C-3″), 26.16 (C-2′), 28.25 (C-15)ⁱ, 29.71 (C-16)ⁱ, 31.66 (C-7), 31.89 (C-4″), 31.94 (C-8), 33.07 (C-3′), 35.46 (C-4′), 36.50 (C-10), 37.36 (C-1), 39.76 (C-12), 40.26 (C-1′), 41.72 (C-2″), 42.30 (C-4)ⁱ, 42.35 (C-13)ⁱ, 50.10 (C-9), 55.91 (C-17), 56.75 (C-14), 69.50 (C-7″), 71.79 (C-3), 82.64 (C-6″), 121.67 (C-6), 140.78 (C-5), 167.39 (C-1″) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-15 / C-16; C-4 / C-13
Specific rotation	[αD] = −20.1 (c = 0.318, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₃₁H₄₈N₃O₂ [M+H]⁺: 494.3747; found: 494.3745
IR ṽ	3311 (s, br), 3299 (s, br), 2934 (s), 2867 (s), 1733 (w), 1651 (s), 1559 (m), 1465 (m), 1443 (m), 1375 (m), 1240 (w, br), 1058 (m), 1023 (w), 958 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethyl (R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-25
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C-18), 0.88 [s, 9H, C3-OSiC(CH3)3], 0.94 (d, J4′,5′ = 6.7 Hz, 3H, C5′-H3) superimposed by 0.90 – 0.96 (m, 1H, C9-H), 0.99 (s, 3H, C-19), 1.02 – 1.98 (m, 5H, C15-HA, C1-HA, C12-HA, C17-H, C14-H), 1.22 – 1.37 (m, 4H, C3′-HA, C16-HA, C2-H2), 1.39 – 1.62 (m, 6H, C4′-H, C15-HB, C8-H, C7-HA, C11-H2), 1.67 (t, J5″,4″ = 7.3 Hz, 2H, C4″-H2), 1.73 (t, J1″,2″ = 6.8 Hz, 2H, C2″-H2), 1.76 – 1.92 (m, 3H, C3′-HB, C16-HB, C1-HB), 1.92 – 2.06 (m, 5H, 7-HB, C5″-H2, C7″-H, C12-HB), 2.16 (mc, 1H, C4-HA), 2.19 – 2.32 (m, 2H, C4-HB, C2′-HA), 2.36 (mc, 1H, C2′-HB), 3.47 (mc, 1H, C3-H), 3.97 (t, J2″,1″ = 6.5 Hz, 2H, C1″-H2), 5.31 (mc, 1H, C6-H) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 57.18 (C3″-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 11.88 (C-18), 13.26 (C-5″), 18.27 (C-5′)ⁱ, 18.33 [C3-OSiC(CH3)3], 19.44 (C-19), 21.06 (C-11)ⁱⁱ, 24.27 (C-15)ⁱⁱ, 25.95 [C3-OSiC(CH3)3], 26.36 (C-3″), 28.13 (C-16), 30.95 (C-3′), 31.18 (C-2′), 31.91 (C-7), 32.09 (C-8)ⁱ, 32.30 (C-2″)ⁱ, 32.33 (C-4″)ⁱ, 35.35 (C-4′), 36.59 (C-10), 37.39 (C-1), 39.78 (C-12), 42.39 (C-13), 42.82 (C-4), 50.17 (C-9), 55.75 (C-17), 56.78 (C-14), 58.90 (C-1″), 69.28 (C-7″), 72.63 (C-3), 82.56 (C-6″), 121.12 (C-6), 141.57 (C-5), 174.04 (C-1′) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 5′-CH3 / C3-OSiC(CH3)3; C-8 / C-2″ / C-4″
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −21.6 (c = 1.07, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₇H₆₄N₃O₃Si [M+NH₄]⁺: 626.4711; found: 626.4651
IR ṽ	3295 (m), 2930 (s), 2903 (s), 2881 (s), 2857 (s), 1734 (s), 1588 (w), 1471 (m), 1459 (m), 1443 (m), 1383 (m), 1368 (m), 1328 (w), 1252 (m), 1220 (w), 1167 (m), 1082 (s), 1025 (w), 1006 (w), 958 (w), 937 (w), 886 (m), 838 (m), 802 (m), 774 (w), 733 (m), 670 (br, w), 637 (br, w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethyl (R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	NBII-165, SPAP I, 5
¹H NMR (400 MHz, CDCl₃, the sample contains traces of CH₂Cl₂ with a signal at δ = 5.31 ppm)	δ = 0.68 (s, 3H, C18-H3), 0.94 (d, J5′,4′ = 7.0 Hz, 3H, C5′-H3) superimposed by 0.85 – 0.97 (m, 1H, C9-H), 1.00 (s, 3H, C19-H3), 1.02 – 1.05 (m, 5H, C1-HA, C12-HA, C14-H, C15-HA, C17-H), 1.26 – 1.34 (m, 1H, C16-HA), 1.39 – 1.58 (m, 7H, C2-H2, C11-H2, C7-HA, C8-H, C15-HB), 1.67 (t, J5″,4″ = 7.6 Hz, 2H, C4″-H2), 1.73 (t, J1″,2″ = 6.5 Hz, 2H, C2″-H2), 1.76 – 1.92 (m, 4H, C1-HB, C3′-H2, C16-HB), 1.97 – 2.05 (m, 4H, C12-HB, C7-HB, C5″-H2), 2.17 – 2.32 (m, 3H, C4-H2, C2′-HA), 2.37 (ddd, ²JAB = 15.4 Hz, J3′A,2′ = 10.3 Hz, J3′B,2′ = 5.2 Hz, 1H, C2′-HB), 3.51 (mc, 1H, C3-H), 3.96 (t, J2″,1″ = 6.5 Hz, 2H, C1″-H2), 5.34 (mc, 1H, C6-H) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.89 (C-18), 13.26 (C-5″), 18.33 (C-5′), 19.40 (C-19), 21.07 (C-11)ⁱⁱ, 24.26 (C-15)ⁱⁱ, 26.37 (C-3″), 28.12 (C-16)ⁱⁱ, 30.94 (C-2)ⁱ,ⁱⁱ, 31.18 (C-7)ⁱ, 31.66 (C-8)ⁱ, 31.88 (C-4″)ⁱ, 31.89 (C-3′)ⁱ, 32.30 (C-2′)ⁱ, 32.33 (C-2″)ⁱ, 35.35 (C-4′), 36.50 (C-10), 37.25 (C-1), 39.75 (C-12), 42.30 (C-13)ⁱ, 42.39 (C-4)ⁱ, 50.08 (C-9), 55.75 (C-17), 56.73 (C-14), 58.91 (C-1″), 69.28 (C-7″), 71.78 (C-3), 82.56 (C-6″), 121.66 (C-6), 140.77 (C-5), 174.04 (C-1′) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-7 / C-8 / C-4″ / C-3′ / C-2′ / C-2″; C-13 / C-4
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −26.7 (c = 1.88, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₁H₅₀N₃O₃ [M+NH₄]⁺: 512.3846; found: 512.3775
IR ṽ	3300 (br), 2936 (s), 2903 (s), 2888 (s), 2867 (s), 2850 (s), 1736 (s), 1589 (w), 1465 (m), 1445 (m), 1376 (m), 1230 (m), 1250 (m), 1166 (m), 1099 (m), 1057 (w), 1024 (m) cm⁻¹

(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-N-[2-(3-methyl-3H-diazirin-3-yl)ethyl]-N-(prop-2-yn-1-yl)pentanamide
Identifier	SPAP VII, 12
¹H NMR (400 MHz, CDCl₃, 58:42 mixture of rotamers)	δ = 0.68 (s, 3H, C18-H3R1/R2), 0.94 (d, J4′,5′ = 6.12 Hz, 3H, C5′-H3R1/R2) superimposed by (m, 1H, C9-HR1/R2), 1.00 (s, 3H, C19-H3R1/R2) superimposed by (m, 1H, C17-HR1/R2), 1.02 – 1.08 (m, 2H, C15-HA;R1/R2, C1-HA;R1/R2) superimposed by 1.05 (s, 3H, C4″-H3R1), 1.07 (s, 3H, C4″-H3R2), 1.11 – 1.21 (m, 2H, C12-HA;R1/R2, C14-HR1/R2), 1.26 – 1.39 (m, 3H, C16-HA;R1/R2, C3′-H2R1/R2), 1.39 – 1.54 (m, 6H, C4′-HR1/R2, C11-H2R1/R2, C8-HR1/R2, C7-HA;R1/R2), 1.57 (mc, 3H, C15-HB;R1/R2, C2″-H2R1), 1.65 (mc, 2H, C2″-H2R2), 1.74 – 1.92 (m, 4H, C16-HB,R1/R2, C1-HB,R1/R2, C2-H2A;R1/R2), 1.92 – 2.05 (m, 2H, C7-HB;R1/R2, C12-HB;R1/R2), 2.13 – 2.37 (m, 4H, C4-H2R1/R2, C3‴-HR1/R2, C2′-HA;R1/R2), 2.42 (mc, 1H, C2′-HB;R1/R2), 3.37 [mc, 2H (0.84H), C1″-H2R2], 3.43 [mc, 2H (1.09H), C1″-H2R1], 3.51 (mc, 1H, C3-HR1/R2), 4.01 [mc, 2H (1.19H), C1‴-H2R1], 4.19 [mc, 2H (0.85H), C1‴-H2R2], 5.34 (mc, 1H, C6-HR1/R2) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 62.46 (C3″-N=NR2), 64.22 (C3″-N=NR1), 114.66 [C1′-NR1/R2] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.90 (C-18)R1/R2, 18.54 (C-5′)R1,ⁱ, 18.56 (C-5′)R2,ⁱ, 19.40 (C-19)R1/R2, 19.58 (C-4″)R1, 19.86 (C-4″)R2, 21.08 (C-11)R1/R2,ⁱⁱ, 23.91 (C-3″)R2, 24.29 (C-15)R1/R2,ⁱⁱ, 24.39 (C-3″)R1, 28.18 (C-16)R1,ⁱⁱ, 28.20 (C-16)R2,ⁱⁱ, 30.05 (C-2′)R2, 30.38 (C-2′)R1, 31.10 (C-3′)R1, 31.33 (C-3′)R2, 31.65 (C-2)R1/R2,ⁱⁱ, 31.87 (C-7)R1/R2,ⁱ, 31.89 (C-8)R1/R2, 32.77 (C-2″)R1, 33.84 (C-2″)R2, 34.14 (C-1‴)R2, 35.54 (C-4′)R1, 35.56 (C-4′)R2, 36.50 (C-10)R1/R2, 37.26 (C-1)R1/R2,ⁱⁱ, 37.81 (C-1‴)R1, 39.76 (C-12)R1/R2, 41.72 (C-1″)R1, 42.09 (C-1″)R2, 42.30 (C-4)R1/R2, 42.40 (C-13)R1/R2, 50.09 (C-9)R1/R2, 55.91 (C-14)R2, 55.95 (C-14)R1, 56.72 (C-17)R1/R2, 71.77 (C-3)R1/R2, 72.03 (C-3‴)R2, 72.77 (C-3‴)R1, 78.58 (C-2‴)R1, 78.99 (C-2‴)R2, 121.67 (C-6)R1/R2, 140.76 (C-5)R1/R2, 172.93 (C-1′)R2, 173.44 (C-1′)R1 ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 5′-CH3R1 / 5′-CH3R2; C-7R1/R2 / C-8R1/R2
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
NMR rotamer qualifier	R1 = rotamer 1, major compound; R2 = rotamer 2, minor compound. The analysis of a NOESY spectrum didn’t result in an unequivocal assignment of the rotamers to a certain structure. Assignment of a signal to either rotamer 1 or 2 was possible due to the respective integrals. Integrals given in brackets correspond to the observed integral in the spectrum
Specific rotation	[αD] = −16.7 (c = 1.03, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₃₁H₄₈N₃O₂ [M+H]⁺: 494.3747; found: 494.3750
IR ṽ	3405 (m, br), 3299 (m, br), 2935 (s), 2866 (s), 1642 (m), 1511 (w, br), 1465 (w), 1378 (m), 1242 (m, br), 1060 (w), 1024 (w), 846 (w) cm⁻¹

(R)-4-{(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}pentan-1-ol
Identifier	19
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C18-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.94 (d, J4′,5′ = 6.6 Hz, 3H, C5′-H3), 1.00 (s, 3H, C19-H3) superimposed by (m, 1H, C9-H)ⁱ, 1.03 – 1.16 (m, 5H, C1-H2, C2-H2, C8-H)ⁱ, 1.17 – 1.31 (m, 3H, C11-H2, C14-H)ⁱ, 1.40 – 1.65 (m, 9H, C12-H2, C15-H2, C16-H2, C3′-H2, C17-H)ⁱ, 1.67 – 1.76 (m, 1H, C4′-H)ⁱ, 1.76 – 1.89 (m, 2H, C7-H2)ⁱ, 1.92 – 2.04 (m, 2H, C2′-H2)ⁱ, 2.16 (ddd, ²J4A,4B = 13.8 Hz, J3,4B = 5.0 Hz, ⁴J6,4B = 2.4 Hz, 1H, C4-HB), 2.26 (mc, 1H, C4-HA), 3.48 (mc, 1H, C3-H), 3.62 (mc, 2H, C1′-H2), 5.31 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked nuclei is interchangeable

(R)-4-{(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}pentyl 2-[3-(but-3-yn-1-yl)-3H-diazirin-3-yl]acetate
Identifier	SI-27
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.67 (s, 3H, C18-H3), 0.88 [s, 9H, C3-OSiC(CH3)3], 0.89 – 0.92 (m, 1H, C9-H), 0.93 (d, J4′,5′ = 6.6 Hz, 3H, C5′-H3), 0.99 (s, 3H, C19-H3), superimposed by 0.96 – 1.01 (m, 1H, C14-H), 1.01 – 1.22 (m, 5H, C16-HA, C3′-HA, C1-HA, C12-HA, C17-H), 1.22 – 1.30 (m, 1H, C15-HA), 1.38 – 1.62 (m, 9H, C11-H2, C16-HB, C2′-HA, C2-HA, C3′-HB, C4′-H, C7-HB, C8-H), 1.65 – 1.75 (m, 2H, C2′-HB, C2-HB), 1.77 (t, J5″,4″ = 7.3 Hz, 2H, C4″-H2) superimposed by 1.76 – 1.87 (m, 2H, C15-HB, C1-HB), 1.98 (t, J5″,7″ = 2.6 Hz, 1H, C7″-H) superimposed by 1.91 – 2.03 (m, 2H, C12-HB, C7-HA), 2.05 (dt, J4″,5″ = 7.4 Hz, J7″,5″ = 2.6 Hz, 2H, C4″-H2), 2.16 (mc, 1H, C4-HA), 2.25 (mc, 1H, C4-HB), 2.32 (s, 2H, C2″-H2), 3.47 (mc, 1H, C3-H), 4.09 (mc, 2H, C1′-H2), 5.31 (mc, 1H, C6-H) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 55.43 (C3″-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 11.87 (C-18), 13.25 (C-5″), 18.28 [C3-OSiC(CH3)3], 18.61 (5′-CH3), 19.44 (C-19), 21.06 (C-11)ⁱⁱ, 24.27 (C-16)ⁱⁱ, 25.15 (C-2′), 25.53 (C-3″), 25.95 [C3-OSiC(CH3)3], 28.21 (C-15)ⁱⁱ, 31.91 (C-2)ⁱ, 31.93 (C-7)ⁱ, 31.96 (C-3′)ⁱ, 32.09 (C-2″, C-8)ⁱ, 35.38 (C-4′), 36.59 (C-10), 37.39 (C-1)ⁱⁱ, 39.78 (C-2″)ⁱ, 39.79 (C-12)ⁱ, 42.36 (C-13), 42.83 (C-4), 50.19 (C-9), 55.87 (C-17), 56.79 (C-14), 65.83 (C-1′), 69.36 (C-7″), 72.64 (C-3), 82.49 (C-6″), 121.12 (C-6), 141.58 (C-5), 169.15 (C-1″) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-7 / C-3′ / C-2″ / C-8; C-2″ / C-12
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −24.8 (c = 0.820, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₇H₆₄N₃O₃Si [M+NH₄]⁺: 626.4711; found: 626.4659
IR ṽ	3309 (m), 3298 (m), 2930 (s), 2903 (s), 2881 (s), 2858 (s), 1736 (s), 1586 (w), 1471 (m), 1460 (m), 1437 (m), 1383 (m), 1367 (m), 1252 (m), 1182 (m, br), 1083 (s), 1025 (w), 1006 (w), 990 (w), 959 (w), 937 (w), 887 (m), 870 (m), 839 (m), 803 (w), 775 (m) cm⁻¹

(R)-4-[(3S,8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentyl 2-[3-(but-3-yn-1-yl)-3H-diazirin-3-yl]acetate
Identifier	SPAP III, 21
¹H NMR (400 MHz, CDCl₃)	δ = 0.70 (s, 3H, C18-H3), 0.96 (d, J4′,5′ = 6.4 Hz, 3H, C5′-H3) superimposed by (m, 2H, C14-H, C9-H), 1.02 (s, 3H, C19-H3), 1.03 – 1.24 (m, 6H, C3′-H2, C17-H, C15-HA, C1-HA, C12-HA), 1.25 – 1.33 (m, 1H, C16-HA), 1.39 – 1.64 (m, 8H, C2′-HA, C4′-H, C15-HB, C8-H, C7-HA, C2-HA, C11-H2)ⁱ, 1.73 (mc, 1H, C2′-HB), 1.80 (t, J5″,4″ = 7.0 Hz, 2H, C4″-H2), 1.82 – 1.92 (m, 3H, C2-HB, C1-HB, C16-HB), 1.95 – 2.05 (m, 2H, C12-HB, C7-HB) superimposed by 2.00 (t, ⁴J5″,7″ = 2.6 Hz, 1H, C7″-H), 2.08 (dt, J4″,5″ = 7.3 Hz, ⁴J7″,5″ = 2.7 Hz, 2H, C5″-H2), 2.20 – 2.33 (m, 2H, C4-H2), 2.34 (s, 2H, C2″-H2), 3.54 (mc, 1H, C3-H), 4.12 (mc, 2H, C1′-H2), 5.37 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁵N NMR (41 MHz, CDCl₃)	δ = 55.43 (C3″-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.88 (C-18), 13.24 (C-5″), 18.60 (5′-CH3), 19.40 (C-19), 21.07 (C-11)ⁱⁱⁱ, 24.26 (C-15)ⁱⁱⁱ, 25.16 (C-2′), 25.53 (C-3″), 28.20 (C-16)ⁱⁱⁱ, 31.66 (C-4″)ⁱⁱ, 31.89 (C-8, C-7)ⁱⁱ, 31.96 (C-2)ⁱⁱ, 32.09 (C-3′)ⁱⁱ, 35.39 (C-4′), 36.50 (C-10), 37.25 (C-1), 39.76 (C-12)ⁱⁱ, 39.77 (C-2″)ⁱⁱ, 42.30 (C-4)ⁱⁱ, 42.35 (C-13)ⁱⁱ, 50.09 (C-9), 55.87 (C-17), 56.74 (C-14), 65.82 (C-1′), 69.37 (C-7″), 71.78 (C-3), 82.49 (C-6″), 121.66 (C-6), 140.78 (C-5), 169.17 (C-1″) ppm
¹³C NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-4″ / C-8 / C-2 / C-3′; C-12 / C-2″; C-4 / C-13
¹³C NMR assignment qualifier iii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −28.8 (c = 0.73, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₁H₅₀N₃O₃ [M+NH₄]⁺: 512.3846; found: 512.3771
IR ṽ	3311 (m, br), 3298 (m, br), 2935 (s), 2903 (s), 2868 (s), 2850 (s), 1737 (s), 1591 (w), 1466 (m), 1445 (m), 1411 (m), 1377 (m), 1188 (m, br), 1059 (w), 1023 (m), 988 (w), 957 (w), 635 (w, br) cm⁻¹

(R)-4-{(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}pentyl 4-methylbenzenesulfonate
Identifier	23
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.64 (s, 3H, C18-H3)ⁱⁱ, 0.86 (d, J4′,5′ = 6.3 Hz, 3H, C5′-H3), 0.89 [s, 9H, C3-OSiC(CH3)3] superimposed by (m, 1H, C9-H)ⁱⁱ, 0.90 – 0.98 (m, 2H, C1-H2)ⁱ, 0.99 (s, 3H, C19-H3), 1.00 – 1.07 (m, 3H, C2-H2, C8-H)ⁱ, 1.07 – 1.22 (m, 2H, C11-H2)ⁱ, 1.31 – 1.43 (m, 3H, C12-H2, C14-H)ⁱ, 1.43 – 1.60 (m, 6H, C15-H2, C16-H2, C3′-H2)ⁱ,ⁱⁱⁱ, 1.65 – 1.76 (m, 3H, C4′-H, C2-H2)ⁱ, 1.80 (mc, 1H, C17-H)ⁱ, 1.92 – 2.00 (m, 2H, C7-H2)ⁱ, 2.16 (ddd, ²J4A,4B = 13.4 Hz, J3,4B = 5.0 Hz, ⁴J6,4B = 2.4 Hz, 1H, C4-HB)ⁱⁱ, 2.26 (mc, 1H, C4-HA)ⁱⁱ, 2.45 (s, 3H, C4″-H3), 3.48 (mc, 1H, C3-H), 4.00 (mc, 2H, C1′-H2), 5.31 (mc, 1H, C6-H), 7.34 (mc, 2H, C3″-H, C5″-H), 7.79 (mc, 2H, C2″-H, C6″-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹H NMR assignment qualifier iii	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement

3-(But-3-yn-1-yl)-3-{2-[((R)-4-{(3S,8S,9S,10R,13R,14S,17R)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}pentyl)oxy]ethyl}-3H-diazirine
Identifier	SI-28
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C18-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.89 – 0.91 (m, 1H, C9-H), 0.93 (d, J4′,5′ = 6.6 Hz, 3H, C5′-H3), 0.99 (s, 3H, C19-H3), 1.00 – 1.22 (m, 6H, C17-H, C15-HA, C14-H, C1-HA, C12-HA, C8-Hⁱ), 1.23 – 1.29 (m, 1H, C15-HA), 1.38 – 1.49 (m, 6H, C2′-HA, C3′-H2ⁱ, C4′-H, C11-H2), 1.51 – 1.73 (m, 5H, C2′-HB, C16-HA, C7-HA, C2-H2ⁱ)ⁱⁱ superimposed by 1.65 (t, J1″,2″ = 6.2 Hz, 2H, C2″-H2) and 1.67 (t, J5″,4″ = 7.8 Hz, 2H, C4″-H2), 1.76 – 1.88 (m, 2H, C15-HB, C1-HB), 1.91 – 2.00 (m, 2H, C7-HA) superimposed by 1.96 (t, ⁴J5″,7″ = 2.6 Hz, 1H, C7″-H), 2.03 (td, J4″,5″ = 7.4 Hz, ⁴J7″,5″ = 2.9 Hz, 2H, C5″-H2) superimposed by (m, 1H, C12-HB), 2.16 (ddd, ²J4B,4A = 13.4 Hz, J3,4 = 5.1 Hz, ⁴J6,4 = 2.2 Hz, 1H, C4-HA), 2.27 (mc, 1H, C4-HB), 3.23 (t, J2″,1″ = 6.3 Hz, 2H, C1″-H2), 3.33 (t, J2′,1′ = 7.0 Hz, 2H, C1′-H2), 3.47 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 11.87 (C-18), 13.32 (C-5″), 18.28 [C3-OSiC(CH3)3], 18.67 (C-5′), 19.44 (C-19), 21.07 (C-11)ⁱⁱⁱ, 24.29 (C-16)ⁱⁱⁱ, 25.95 [C3-OSiC(CH3)3], 26.19 (C-2′), 26.95 (C-3″), 28.22 (C-15)ⁱⁱⁱ, 31.92 (C-7)ⁱ, 31.94 (C-8)ⁱ, 32.10 (C-2)ⁱ, 32.20 (C-3′)ⁱ, 32.78 (C-2″), 33.20 (C-4″), 35.58 (C-4′), 36.60 (C-10), 37.39 (C-1), 39.80 (C-12), 42.35 (C-1″), 68.96 (C-7″), 71.75 (C-1′), 72.66 (C-3), 82.92 (C-6″), 121.16 (C-6), 141.59 (C-5) ppm
NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 8-H / 3′-CH2 / 2-CH2; C-7 / C-8; C-2 / C-3′
¹H NMR assignment qualifier ii	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹³C NMR assignment qualifier iii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −19.5 (c = 0.25, CHCl₃)
IR ṽ	3310 (w), 2929 (s), 2855 (s), 1730 (w), 1586 (w), 1461 (m), 1444 (m), 1380 (m), 1368 (m), 1252 (m), 1083 (s), 1025 (w), 1006 (w), 959 (w), 937 (w), 887 (m), 869 (m), 836 (m), 803 (w), 774 (m), 668 (w), 633 (w) cm⁻¹

(3S,8S,9S,10R,13R,14S,17R)-17-{(R)-5-{2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethoxy}pentan-2-yl}-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Identifier	SPAP IX, 25
¹H NMR (400 MHz, CDCl₃)	δ = 0.68 (s, 3H, C18-H3), 0.93 (d, J4′,5′ = 6.3 Hz, 3H, C5′-H3) superimposed by (m, 2H, C9-H, C14-H), 1.00 (s, 3H, C19-H3), 1.03 – 1.20 (m, 5H, C1-HA, C7-HA, C12-HA, C15-HA, C17-H), 1.21 – 1.32 (m, 2H, C8-H, C16-HA), 1.37 – 1.62 (m, 9H, C2′-H2, C3′-H2, C4′-H, C15-HB, C1-HA, C11-H2)ⁱ, 1.65 (t, J1″,2″ = 6.3 Hz, 2H, C2″-H2), 1.67 (t, J5″,4″ = 7.8 Hz, 2H, C4″-H2), 1.78 – 1.89 (m, 3H, C16-HB, C1-HB, C2-HB), 1.93 – 2.06 (m, 2H, C7-HB, C12-HB) superimposed by (t, ⁴J5″,7″ = 2.5 Hz, 1H, C7″-H) and (dt, J4″,5″ = 7.5 Hz, ⁴J7″,5″ = 2.5 Hz, 2H, C5″-H2), 2.17 – 2.33 (m, 2H, C4-H2), 3.32 (t, J2″,1″ = 6.4 Hz, 2H, C1″-H2), 3.33 (mc, 2H, C1′-H2), 3.52 (mc, 1H, C3-H), 5.35 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁵N NMR (41 MHz, CDCl₃)	δ = 58.16 (C3″-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.88 (C-18), 13.32 (C-5″), 18.67 (C-5′), 19.41 (C-19), 21.08 (C-11), 24.29 (C-15), 26.20 (C-2′), 26.95 (C-3″), 28.21 (C-16), 29.71 (C-8), 31.67 (C-2), 31.90 (C-7), 32.20 (C-3′), 32.78 (C-4″)ⁱⁱ, 33.20 (C-2″), 35.58 (C-4′), 36.51 (C-10), 37.26 (C-1), 39.77 (C-12), 42.31 (C-4)ⁱⁱ, 42.33 (C-13)ⁱⁱ, 50.11 (C-9), 55.97 (C-17), 56.76 (C-14), 65.10 (C-1′), 68.97 (C-7″), 71.75 (C-1″), 71.81 (C-3), 82.92 (C-6″), 121.70 (C-6), 140.77 (C-5) ppm
¹³C NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-4″ / C-2″; C-4 / C-13
Specific rotation	[αD] = −36.0 (c = 0.382, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₁H₅₂N₃O₂ [M+NH₄]⁺: 498.4054; found: 498.3982
IR ṽ	3406 (m, br), 3303 (m), 2936 (s), 2902 (s), 2866 (s), 1732 (w), 1585 (w), 1465 (m), 1446 (m), 1435 (m), 1375 (m), 1365 (m), 1114 (m), 1058 (m), 1023 (w), 986 (w), 958 (w), 839 (w), 741 (w) cm⁻¹

(3S,8S,9S,10R,13S,14S,17S)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
Identifier	SI-29
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.73 (s, 3H, C19-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.91 – 1.02 (m, 1H, C9-H) superimposed by 1.01 (s, 3H, C20-H3), 1.03 – 1.13 (m, 2H, C14-H, C1-HA), 1.21 – 1.33 (m, 2H, C16-HA, C12-HA), 1.42 – 1.64 (m, 5H, C8-H, C7-HA, C2-HA, C11-H2), 1.67 – 1.84 (m, 4H, C16-HB, C15-HA, C2-HB, C1-HB), 1.96 – 2.05 (m, C12-HB, C7-HB), 2.10 – 2.20 (m, 3H, C17-H, C15-HB, C4-HA), 2.20 – 2.31 (m, 1H, C4-HB), 3.48 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H) superimposed by (br. s, 1H, C18-NH), 5.52 (br. s, 1H, C18-NH) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 12.91 (C-19), 18.27 [C3-OSiC(CH3)3], 19.45 (C-20), 21.00 (C-11), 23.67 (C-15), 24.53 (C-16), 25.94 [C3-OSiC(CH3)3], 31.84 (C-7), 31.97 (C-8), 32.05 (C-2), 36.65 (C-10), 37.42 (C-1), 38.41 (C-12), 42.78 (C-4), 43.67 (C-13), 50.17 (C-9), 56.52 (C-17)ⁱ, 56.54 (C-14)ⁱ, 72.55 (C-3), 120.85 (C-6), 141.59 (C-5), 175.34 (C-18) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-17 / C-14
Specific rotation	[αD] = −37.1 (c = 0.3077, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₆H₄₆NO₂Si [M+H]⁺: 432.3298; found: 432.3303
IR ṽ	3311 (br), 2961 (s), 2932 (s), 2902 (s), 2856 (s), 2359 (s), 2341 (br, m), 1682 (s), 1637 (s), 1436 (m, br), 1383 (m), 1260 (s), 1207 (s), 1181 (m), 1135 (s), 1087 (s), 888 (w), 870 (w), 840 (w), 801 (s), 724 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]-N-{[(3S,8S,9S,10R,13S,14S,17S)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]methyl}acetamide
Identifier	SI-30
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.68 (s, 3H, C19-H3), 0.88 [s, 9H, C3-OSiC(CH3)3], 0.91 – 1.10 (m, 3H, C14-H, C1-HA, C9-H), 1.11 – 1.21 (m, 2H, C15-HA, C12-HA), 1.30 – 1.36 (m, 1H, C16-HA), 1.45 – 1.61 (m, 6H, C17-H, C7-HA, C2-HA, C11-H2, C8-H), 1.63 – 1.73 (m, 2H, C15-HB, C2-HB), 1.77 (t, J5″,4″ = 7.3 Hz, 2H, C4″-H2), 1.78 – 1.89 (m, 2H, C16-HB, C1-HB), 1.93 – 1.98 (m, 1H, C7-HB), 2.00 (t, ⁴J5″,7″ = 2.6 Hz, 1H, C7″-H), 2.07 (td, J4″,5″ = 7.3 Hz, ⁴J7″,5″ = 2.7 Hz, 2H, C5″-H2), 2.16 (mc, 1H, C4-HA), 2.22 (d, ⁴JNH,2″ = 2.1 Hz, 2H, C2″-H2), 2.22 – 2.31 (m, 1H, C4-HB), AB signal (δA = 3.17, δB = 3.36, ²JAB = 13.7 Hz, additional splitting A: J17,A = 8.7 Hz, JNH,A = 5.5 Hz; additional splitting B: J17,B = 5.8 Hz, JNH,B = 5.8 Hz, 2H, C18-H2), 3.47 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H), 5.62 (br. m, 1H, C18-NH) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 56.01 (C3′-N=N), 118.57 [C1′-NH] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.58 [C3-OSi(CH3)2], 12.52 (C-19), 13.30 (C-5″), 18.27 [C3-OSiC(CH3)3], 19.45 (C-20), 20.79 (C-11)ⁱ, 24.52 (C-15)ⁱ, 25.94 [C3-OSiC(CH3)3], 26.06 (C-3″), 26.27 (C-16), 31.72 (C-8), 31.89 (C-4″)ⁱⁱ, 31.91 (C-7)ⁱⁱ, 32.07 (C-2)ⁱⁱ, 36.67 (C-10), 37.42 (C-1), 38.18 (C-12), 41.03 (C-18), 41.74 (C-13), 41.82 (C-2″), 42.82 (C-4), 50.12 (C-17), 50.41 (C-9), 56.11 (C-14), 69.49 (C-7″), 72.58 (C-3), 82.62 (C-6″), 120.93 (C-6), 141.63 (C-5), 167.35 (C-1″) ppm
¹³C NMR assignment qualifier i	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹³C NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-4″ / C-7 / C-2
Specific rotation	[αD] = −28.0 (c = 0.500, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₃H₅₄N₃O₂Si [M+H]⁺: 552.3980; found: 552.3919
IR ṽ	3295 (s), 3091 (w, br), 2929 (s), 2901 (s), 2885 (s), 2856 (s), 1762 (w), 1737 (w), 1641 (s), 1558 (m), 1471 (m), 1461 (m), 1446 (m), 1435 (m), 1381 (m), 1365 (m), 1333 (w), 1252 (m), 1222 (w), 1197 (w), 1129 (w), 1094 (s), 1054 (w), 1024 (w), 1006 (w), 985 (w), 958 (w), 938 (w), 886 (m), 870 (m), 837 (m), 803 (w), 775 (m), 735 (w), 669 (w), 638 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]-N-{[(3S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]methyl}acetamide
Identifier	SPAP VI, 18
¹H NMR (400 MHz, CDCl₃)	δ = 0.92 – 0.99 (m, 1H, C9-H)ⁱ, 1.01 (s, 3H, C19-H3) superimposed by 0.99 – 1.10 (m, 2H, C14-H, C1-HA), 1.10 – 1.28 (m, 2H, C15-HA, C12-HA), 1.30 – 1.38 (m, 1H, C16-HA), 1.46 – 1.60 (m, 6H, C2-HA, C7-HA, C8-H, C11-H2, C17-H)ⁱ, 1.62 – 1.72 (m, 1H, C15-HB), 1.77 (t, J5′,4′ = 7.5 Hz, 2H, C4′-H2), 1.79 – 1.91 (m, 4H, C1-HB, C7-HB, C12-HB, C16-HB), 1.94 – 1.99 (m, 1H, C2-HB), 2.00 (t, J5′,7′ = 2.6 Hz, 1H, C7′-H), 2.07 (mc, 2H, C5′-H2), 2.22 (d, JNH,18 = 2.2 Hz, 2H, C2′-H2) superimposed by 2.19 – 2.34 (m, 2H, C4-H2), 3.17 (ddd, ²JA,B = 13.8 Hz, J17,18B = 8.6 Hz, JNH,18B = 5.5 Hz, 1H, C18-HB)ⁱ, 3.36 (ddd, ²JB,A = 13.4 Hz, J17,18A = 5.5 Hz, JNH,18A = 5.5 Hz, 1H, C18-HA)ⁱ, 3.53 (mc, 1H, C3-H), 5.35 (mc, 1H, C6-H), 5.63 (mc, 1H, C18-NH) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 56.21 (C3′-N=N), 118.57 [C1′-NH] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 12.53 (C-19), 13.30 (C-7′), 19.42 (C-20), 20.80 (C-11), 24.52 (C-15), 26.06 (C-3′), 26.72 (C-16), 31.65 (C-2)ⁱ, 31.71 (C-7)ⁱ, 31.87 (C-8)ⁱ, 31.95 (C-4′)ⁱ, 36.58 (C-10), 37.29 (C-1), 38.14 (C-12), 41.02 (C-18), 41.74 (C-13)ⁱ, 41.81 (C-2′)ⁱ, 42.28 (C-4), 50.12 (C-9)ⁱ, 50.32 (C-17)ⁱ, 56.07 (C-14), 69.49 (C-7′), 71.74 (C-3), 82.63 (C-6′), 121.47 (C-6), 140.83 (C-5), 167.36 (C-1′) ppm
NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 9-H / 17-H; C2-HA / C2-HB / 7-HA / 7-HB; 18-HA / 18-HB; C-2 / C-7 / C-8 / C-4′; C-13 / C-2′; C-9 / C-17
Specific rotation	[αD] = −50.0 (c = 0.272, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₂₇H₄₀N₃O₂ [M+H]⁺: 438.3121; found: 438.3125
IR ṽ	3308 (s, br), 3089 (w), 2934 (s), 2902 (s), 2868 (s), 2850 (s), 1649 (s), 1558 (m), 1465 (m), 1436 (m), 1376 (m), 1294 (br), 1246 (br), 1193 (br), 1052 (w), 954 (m), 839 (w), 801 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethyl (3S,9S,10R,13S,14S,17S)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
Identifier	SI-31
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.69 (s, 3H, C19-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 1.00 (s, 3H, C20-H3) superimposed by 0.92 – 1.02 (m, 1H, C9-H), 1.03 – 1.16 (m, 2H, C14-H, C16-HA), 1.21 – 1.35 (m, 2H, C15-HA, C12-HA), 1.42 – 1.64 (m, 5H, C2-H2, C11-H2, C8-H), 1.68 (t, J5′,4′ = 7.4 Hz, 2H, C4′-H2), 1.75 (t, J1′,2′ = 6.5 Hz, 2H, C2′-H2) superimposed by 1.68 – 1.74 (m, 2H, C15-HB, C5′-HA), 1.78 – 1.87 (m, 2H, C16-HB, C1-HA), 1.95 – 2.05 (m, 4H, C5′-HB, C7-H2, C7′-H), 2.08 (mc, 1H, C12-HB), 2.10 – 2.16 (m, 1H, C1-HB), 2.19 (mc, 1H, C4-HA), 2.22 – 2.32 (m, 1H, C4-HB), 2.36 (dd, J16A,17 = 9.4 Hz, J16B,17 = 9.4 Hz, 1H, C17-H), 3.48 (mc, 1H, C3-H), 3.97 (mc, 2H, C1′-H2), 5.31 (mc, 1H, C6-H) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 13.28 (C-5″), 13.35 (C-19), 18.27 [C3-OSiC(CH3)3], 19.45 (C-20), 20.94 (C-11)ⁱ, 23.67 (C-1), 24.56 (C-15), 25.94 [C3-OSiC(CH3)3], 26.36 (C-3′), 31.87 (C-4′)ⁱ, 32.03 (C-2′)ⁱ, 32.07 (C-8)ⁱ, 32.29 (C-7)ⁱ, 32.44 (C-2)ⁱ, 36.66 (C-10), 37.41 (C-16), 38.25 (C-12), 42.79 (C-4), 44.08 (C-13), 50.17 (C-9), 55.22 (C-17), 56.29 (C-14), 58.68 (C-1′), 69.28 (C-7′), 72.56 (C-3), 82.56 (C-6′), 120.84 (C-6), 141.65 (C-5), 173.91 [17-CHC(O)O] ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-11 / C-2; C-4′ / C-2′ / C-8 / C-7 / C-2
Specific rotation	[αD] = −11.5 (c = 0.666, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₆₆H₁₀₄N₄O₆Si₂Na [2M+Na]⁺: 1127.7387; found: 1127.7385
IR ṽ	3311 (br.), 2958 (s), 2938 (s), 2898 (s), 2854 (s), 2361 (m), 2337 (w), 2034 (w), 1717 (m), 1680 (m), 1459 (w), 1417 (w), 1383 (w), 1367 (w), 1256 (m), 1088 (m), 1064 (m), 1026 (m), 887 (w), 872 (w), 836 (w), 803 (w), 770 (w) cm⁻¹

2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethyl (3S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
Identifier	SPAP II, 13
¹H NMR (400 MHz, CDCl₃)	δ = 0.72 (s, 3H, C18-H3), 0.96 – 1.04 (m, 1H, C9-H) superimposed by 1.03 (s, 3H, C19-H3), 1.05 – 1.19 (m, 2H, C14-H, C1-HA), 1.24 – 1.34 (m, 2H, C15-HA, C12-HA), 1.44 – 1.57 (m, 3H, C8-H, C11-HA, C2-HA), 1.57 – 1.67 (m, 2H, C11-HB, C7-HA), 1.70 (t, J5′,4′ = 7.3 Hz, 2H, C4′-H2), 1.77 (t with further not definable splitting, J1′,2′ = 6.2 Hz, 2H, C2′-H2) superimposed by 1.73 – 1.80 (m, 1H, C15-HB), 1.82 – 1.92 (m, 3H, C2-HB, C1-HB, C16-HA), 1.98 – 2.07 (m, 4H, C5′-H2, C7-HB, C7″-H), 2.07 – 2.23 (m, 2H, C16-HB, C12-HB), 2.26 (mc, 1H, C4-HA), 2.32 (mc, 1H, C4-HB), 2.38 (dd, J16A,17 = 9.3 Hz, J16B,17 = 9.3 Hz, 1H, C17-H), 3.54 (mc, 1H, C3-H), 3.98 (mc, 2H, C1′-H2), 5.37 (mc, 1H, C6-H) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 57.18 (C3′-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 13.28 (C-5′), 13.35 (C-18), 19.42 (C-19), 20.96 (C-11), 23.67 (C-16), 24.55 (C-15), 26.36 (C-3′), 31.64 (C-2)ⁱ, 31.82 (C-8)ⁱ, 32.02 (C-7)ⁱ, 32.29 (C-2′)ⁱ, 32.43 (C-4′)ⁱ, 36.57 (C-10), 37.27 (C-1), 38.21 (C-12), 42.26 (C-4), 44.06 (C-13), 50.07 (C-9), 55.21 (C-17), 56.24 (C-14), 58.69 (C-1′), 69.28 (C-7′), 82.56 (C-6′), 121.38 (C-6), 140.85 (C-5)ⁱⁱⁱ, 173.89 (C-20) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-8 / C-7 / C-2′ / C-4′
Specific rotation	[αD] = −11.9 (c = 0.31, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₂₇H₄₂N₃O₃ [M+NH₄]⁺: 456.3220; found: 456.3140
IR ṽ	3274 (s, br), 2963 (s), 2925 (s), 2902 (s), 2854 (s), 1727 (s), 1585 (w), 1450 (m), 1438 (m), 1385 (m), 1353 (m), 1293 (w), 1230 (m), 1189 (m), 1162 (m), 1148 (m), 1133 (m), 1063 (m), 991 (w), 955 (w), 652 (w, br) cm⁻¹

(3S,9S,10R,13S,14S,17S)-3-Hydroxy-10,13-dimethyl-N-[2-(3-methyl-3H-diazirin-3-yl)ethyl]-N-(prop-2-yn-1-yl)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-17-carboxamide
Identifier	SPAP VIII, 14
¹H NMR (400 MHz, CDCl₃, 63:37 mixture of rotamers)	δ = 0.74 (s, 3H, C18-H3R1/R2), 0.92 – 1.04 (m, 1H, C9-HR1/R2) superimposed by (s, 3H, C19-H3R1/R2), 1.06 (s, 3H, C4′-H3R1/R2) superimposed by (m, 1H, C1-HA,R1/R2), 1.14 – 1.21 (m, 1H, C14-HR1/R2), 1.26 – 1.39 (m, 2H, C15-HA,R1/R2, C12-HA,R1/R2), 1.43 – 1.67 (m, 8H, C2′-CH2R1/R2, C7-HA,R1/R2, C2-HA,R1/R2, C11-H2R1/R2), 1.66 – 1.77 (m, 2H, C15-HB,R1/R2, C16-HA,R1/R2), 1.77 – 1.87 (m, 2H, C2-HB,R1/R2, C1-HB,R1/R2), 1.91 (mc, 1H, C12-HB,R2), 2.01 (mc, 1H, C12-HB,R1), 2.17 – 2.33 (m, 4H, C3″-HR1/R2, C16-HB,R1/R2, C4-H2R1/R2), 2.58 [br. dd, J16A,17 = 8.8 Hz, J16B,17 = 8.8 Hz, 1H (0.37H), C17-HR2], 2.70 [br. dd, J16A,17 = 8.7 Hz, J16B,17 = 8.7 Hz, 1H (0.60H), C17-HR1], 3.19 – 3.31 (m, 1H, C1′-HA,R1/R2), 3.52 (mc, 1H, C3-HR1/R2), 3.58 – 3.73 (m, 1H, C1′-HB,R1/R2), 3.89 [dd, ²J1′A,1′B = 18.4 Hz, ⁴J1′A,3′ = 2.5 Hz, 1H (0.6H), C1′-HA,R1], 3.92 [dd, ²J1′B,1′A = 17.6 Hz, ⁴J1′B,3′ = 2.2 Hz, 1H (0.4H), C1′-HA,R2], 4.33 [dd, ⁴J1′B,1′A = 18.1 Hz, ²J1′B,3′ = 1.7 Hz, 1H (0.6H), C1′-HB,R1], 4.48 [dd, ⁴J1′A,1′B = 17.7 Hz, ²J1′B,3′ = 1.9 Hz, 1H (0.4H), C1′-HB,R2], 5.34 (mc, 1H, C6-HR1/R2) ppm
¹⁵N NMR (41 MHz, CDCl₃)	δ = 62.85 (C3′-N=NR1)ⁱⁱ, 64.61 (C3′-N=NR2)ⁱⁱ, 117.30 [C17-NR1/R2] ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 13.68 (C-18)R1, 13.76 (C-18)R2, 19.39 (C-19)R1/R2, 19.55 (C-4′)R1, 19.96 (C-4′)R2, 21.11 (C-11)R1/R2,ⁱ, 23.98 (C-3′)R2, 24.49 (C-3′)R1, 24.74 (C-15)R1,ⁱ, 24.78 (C-15)R1,ⁱ, 25.79 (C-16)R1, 25.90 (C-16)R2, 31.62 (C-2)R1/R2,ⁱ, 31.89 (C-7)R1/R2,ⁱ, 32.03 (C-8)R1/R2,ⁱ, 32.91 (C-2′)R1, 33.89 (C-2′)R2, 34.47 (C-1″)R2, 36.57 (C-10)R1/R2, 37.30 (C-1)R1/R2, 37.88 (C-1″)R1, 38.87 (C-12)R1, 39.14 (C-12)R2, 41.84 (C-1′)R1, 42.10 (C-1′)R2, 42.26 (C-4)R1/R2, 45.19 (C-13)R1, 45.41 (C-13)R2, 50.02 (C-9)R2, 50.08 (C-9)R1, 51.39 (C-17)R2, 51.49 (C-17)R1, 56.75 (C-14)R1/R2, 71.69 (C-3)R1/R2, 71.78 (C-3″)R2, 72.62 (C-3″)R1, 78.88 (C-2″)R1, 79.44 (C-2″)R2, 121.43 (C-6)R1/R2, 140.76 (C-5)R1/R2, 172.95 [17-C(O)]R2, 173.30 [17-C(O)]R1 ppm
¹³C NMR assignment qualifier i	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹⁵N NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the all marked nuclei is interchangeable
NMR rotamer qualifier	R1 = rotamer 1, major compound; R2 = rotamer 2, minor compound. The analysis of a NOESY spectrum didn’t result in an unequivocal assignment of the rotamers to a certain structure. Assignment of a signal to either rotamer 1 or 2 was possible due to the respective integrals. Integrals given in brackets correspond to the observed integral in the spectrum
Specific rotation	[αD] = −58.5 (c = 0.982, CHCl₃)
HRMS m/z (pos. ESI TIC)	Calcd. for C₂₇H₄₀N₃O₂ [M+H]⁺: 438.3121; found: 438.3123
IR ṽ	3446 (m, br), 3310 (m, br), 3300 (m, br), 2932 (s), 2901 (s), 2849 (s), 1637 (s), 1449 (m), 1436 (m), 1386 (m), 1309 (w), 1234 (m), 1209 (m), 1133 (w), 1059 (m), 1028 (w), 955 (w), 840 (w) cm⁻¹

[(3S,9S,10R,13S,14S,17S)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]methanol
Identifier	20
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.66 (s, 3H, C19-H3)ⁱ, 0.89 [s, 9H, C3-OSiC(CH3)3], 0.96 (mc, 1H, C9-H)ⁱ, 1.01 (s, 3H, C20-H3), 1.02 – 1.10 (m, 2H, C12-H2)ⁱⁱ, 1.11 – 1.35 (m, 4H, C1-H2, C2-H2)ⁱⁱ, 1.39 – 1.60 (m, 4H, C7-H2, C16-HB, C8-H)ⁱⁱ, 1.62 – 1.76 (m, 3H, C11-H2, C14-H)ⁱⁱ, 1.78 – 1.91 (m, 3H, C15-H2, C16-HA)ⁱⁱ, 1.98 (mc, 1H, C17-H)ⁱ, 2.17 (ddd, ²J4B,4A = 13.3 Hz, J3,4A = 5.1 Hz, J6,4A = 2.3 Hz, 1H, C4-HA)ⁱ, 2.27 (mc, 1H, C4-HB)ⁱ, 3.48 (mc, 1H, C3-H), AB signal (δA = 3.55, δB = 3.73, JAB = 10.4 Hz, additional splitting: J17,18A = 7.5 Hz, J17,18B = 6.8 Hz, 2H, C18-H2), 5.31 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹H NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable

{(3S,9S,10R,13S,14S,17S)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}methyl 2-[3-(but-3-yn-1-yl)-3H-diazirin-3-yl]acetate
Identifier	SI-33
¹H NMR (400 MHz, CDCl₃)	δ = 0.05 [s, 6H, C3-OSi(CH3)2], 0.67 (s, 3H, C19-H3), 0.88 [s, 9H, C3-OSiC(CH3)3], 0.90 – 1.09 (m, 3H, C14-H, C9-H, C1-HA) superimposed by 1.00 (s, 3H, C20-H3), 1.11 – 1.21 (m, 2H, C15-HA, C12-HA)ⁱⁱ, 1.28 – 1.36 (m, 1H, C16-HA), 1.40 – 1.61 (m, 5H, C7-HA, C2-HA, C8-H, C11-H2)ⁱ,ⁱⁱ, 1.62 – 1.89 (m, 6H, C17-H, C16-HB, C15-HB, C7-HB, C1-HB, C12-HB)ⁱⁱ superimposed by (t, J5′,4′ = 7.6 Hz, 2H, C4′-H2), 1.94 – 2.07 (m, 1H, C2-HB) superimposed by 1.98 (t, ⁴J5′,7′ = 2.5 Hz, 1H, C7′-H) and 2.05 (td, J4′,5′ = 7.6 Hz, ⁴J5′,7′ = 2.6 Hz, 2H, C5′-H2), 2.16 (ddd, ²J4A,4B = 13.4 Hz, J3,4B = 5.1 Hz, ⁴J6,4 = 2.4 Hz, 1H, C4-HB), 2.22 – 2.32 (m, 1H, C4-HA) superimposed by 2.31 (s, 2H, C2′-H2), 3.48 (mc, 1H, C3-H), 4.11 (mc, 2H, C18-H2), 5.31 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 2-CH2 / 7-CH2
¹H NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹⁵N NMR (41 MHz, CDCl₃)	δ = 55.62 (C3′-N=N) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = −4.58 [C3-OSi(CH3)2], 12.43 (C-19), 13.24 (C-5′), 18.27 [C3-OSiC(CH3)3], 19.46 (C-20), 20.77 (C-11)ⁱⁱ, 24.58 (C-15)ⁱⁱ, 25.53 (C-16, C-3′), 25.94 [C3-OSiC(CH3)3], 31.68 (C-8), 31.93 (C-7)ⁱ, 32.07 (C-2, C-4′)ⁱ, 36.67 (C-10), 37.41 (C-1), 38.24 (C-12), 39.80 (C-2′), 41.81 (C-13), 42.82 (C-4), 48.80 (C-17), 50.39 (C-9), 56.12 (C-14), 66.71 (C-18), 69.36 (C-7′), 72.58 (C-3), 82.50 (C-6′), 120.94 (C-6), 141.63 (C-5), 169.19 (C-1′) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: 2-CH2 / 7-CH2
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
Specific rotation	[αD] = −32.8 (c = 0.865, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₃₃H₅₆N₃O₃Si [M+NH₄]⁺: 570.4085; found: 570.4023
IR ṽ	3312 (w), 2934 (s), 2902 (s), 2854 (s), 2365 (m), 2357 (m), 2338 (w), 1738 (s), 1540 (w), 1472 (m), 1448 (m), 1436 (m), 1382 (m), 1361 (m), 1342 (m), 1252 (m), 1180 (m), 1093 (m), 1055 (s), 1005 (w), 959 (w), 938 (w), 888 (w), 871 (m), 836 (m), 817 (m), 805 (w), 775 (w), 716 (m) cm⁻¹

[(3S,9S,10R,13S,14S,17S)-3-Hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]methyl 2-[3-(but-3-yn-1-yl)-3H-diazirin-3-yl]acetate
Identifier	SPAP IV, 22
¹H NMR (400 MHz, CDCl₃)	δ = 0.68 (s, 3H, C19-H3), 1.01 (s, 3H, C20-H3) superimposed by 0.92 – 1.02 (m, 1H, C9-H), 1.02 – 1.37 (m, 6H, C16-HA, C15-HA, C14-H, C1-H2, C12-HA), 1.42 – 1.62 (m, 5H, C8-H, C7-HA, C2-HA, C11-H2)ⁱ, 1.64 – 1.73 (m, 1H, C15-HB), 1.77 (t, J5′,4′ = 7.9 Hz, 2H, C4′-H2) superimposed by (m, 1H, C17-H), 1.81 – 1.88 (m, 3H, C16-HB, C12-HB, C2-HB), 1.99 (t, ⁴J5′,7′ = 2.7 Hz, 1H, C7′-H) superimposed by (m, 1H, C7-HB), 2.05 (dt, J4′,5′ = 7.7 Hz, ⁴J7′,5′ = 2.5 Hz, 2H, C5′-H2), 2.18 – 2.33 (m, 2H, C4-H2) superimposed by (s, 2H, C2′-CH2), 3.52 (mc, 1H, C3-H), 4.11 (mc, 2H, C18-H2), 5.40 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁵N NMR (41 MHz, CDCl₃)	δ = 55.62 ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 12.44 (C-19), 13.24 (C-5′), 19.43 (C-20), 20.78 (C-11), 24.57 (C-15), 25.51 (C-16), 25.54 (C-3′), 31.66 (C-8, C-7)ⁱⁱ, 31.89 (C-2)ⁱⁱ, 32.07 (C-4′)ⁱⁱ, 36.58 (C-10), 37.28 (C-1), 38.21 (C-12), 39.80 (C-2′), 41.80 (C-13), 42.28 (C-4), 48.79 (C-17), 50.30 (C-9), 56.08 (C-14), 66.70 (C-18), 69.37 (C-7′), 71.74 (C-3), 82.50 (C-6′), 121.48 (C-6), 140.84 (C-5), 169.20 (C-1′) ppm
¹³C NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-7 / C-4′
Specific rotation	[αD] = −48.5 (c = 0.827, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₇H₄₂N₃O₃ [M+NH₄]⁺: 456.3220; found: 456.3144
IR ṽ	3372 (m, br), 3300 (m, br), 2935 (s), 2902 (s), 2869 (s), 2851 (s), 1736 (s), 1584 (w), 1465 (m), 1448 (m), 1437 (m), 1411 (m), 1377 (m), 1357 (m), 1229 (m), 1182 (m), 1134 (m), 1109 (m), 838 (w), 804 (w), 634 (w, br) cm⁻¹

{(3S,9S,10R,13S,14S,17S)-3-[(tert-Butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl}methyl trifluoromethanesulfonate
Identifier	24
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.71 (s, 3H, C19-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 1.00 (s, 3H, C20-H3) superimposed by (m, 1H, C9-H)ⁱ, 1.02 – 1.14 (m, 2H, C1-H2)ⁱ, 1.14 – 1.28 (m, 3H, C15-H2, C17-H)ⁱ, 1.30 – 1.40 (m, 1H, C8-H)ⁱ, 1.40 – 1.62 (m, 3H, C16-H2, C14-H)ⁱ,ⁱⁱ, 1.68 – 2.04 (m, 8H, C2-H2, C7-H2, C11-H2, C12-H2)ⁱ, 2.17 (ddd, ²J4B,4A = 13.5 Hz, J3,4A = 5.0 Hz, ⁴J6,4A = 2.3 Hz, 1H, C4-HA), 2.27 (mc, 1H, C4-HB), 3.48 (mc, 1H, C3-H), AB signal (δA = 4.47, δB = 4.57, JAB = 9.7 Hz, additional splitting: J17,A = 6.9 Hz, J17,B = 7.6 Hz, 2H, C18-H2), 5.31 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable
¹H NMR assignment qualifier ii	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁹F NMR (376.5 MHz, CDCl₃, spectrum contains an impurity with a signal at δ = −78.3 ppm)	δ = −74.8 ppm

3-(But-3-yn-1-yl)-3-(2-{[(3S,9S,10R,13S,14S,17S)-3-[(tert-butyldimethylsilyl)oxy]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]methoxy}ethyl)-3H-diazirine
Identifier	SI-34
¹H NMR (400 MHz, CDCl₃)	δ = 0.06 [s, 6H, C3-OSi(CH3)2], 0.64 (s, 3H, C19-H3), 0.89 [s, 9H, C3-OSiC(CH3)3], 0.90 – 1.09 (m, 3H, C14-H, C9-H, C1-HA) superimposed by 1.00 (s, 3H, C20-H3), 1.09 – 1.20 (m, 2H, C16-HA, C12-HA), 1.23 – 1.33 (m, 1H, C15-HA)ⁱ, 1.35 – 1.60 (m, 5H, C8-H, C7-HA, C11-H2, C2-HA), 1.61 – 1.75 (m, 7H, C4′-H2, C2′-H2, C17-H, C16-HB, C2-HA), 1.76 – 1.86 (m, 2H, C1-HB, C15-HB), 1.90 (mc, 1H, C12-HB), 1.94 – 2.06 (m, 1H, C7-HB) superimposed by 1.96 (t, ⁴J5′,7′ = 2.6 Hz, 1H, C7′-H) and 2.03 (td, J4′,5′ = 7.4 Hz, ⁴J7′,5′ = 2.5 Hz, 2H, C5′-H2), 2.16 (ddd, ²J4B,4A = 13.0 Hz, J3,4A = 5.0 Hz, ⁴J6,4A = 2.3 Hz, 1H, C4-HA), 2.27 (mc, 1H, C4-HB), 3.22 (t, J2′,1′ = 6.5 Hz, 2H, C1′-H2), AB signal (δA = 3.24, δB = 3.43, JAB = 9.5 Hz, additional splitting: J17,A = 7.5 Hz, J17,B = 6.5 Hz, 2H, C18-H2), 3.48 (mc, 1H, C3-H), 5.31 (mc, 1H, C6-H) ppm
¹H NMR assignment qualifier i	Superimposed by a signal originating from an unknown impurity
¹³C NMR (100 MHz, CDCl₃)	δ = −4.57 [C3-OSi(CH3)2], 12.36 (C-19), 13.38 (C-5′), 18.28 [C3-OSiC(CH3)3], 19.47 (C-20), 20.82 (C-11)ⁱⁱ, 24.72 (C-16), 25.95 [C3-OSiC(CH3)3], 26.02 (C-15), 27.00 (C-3′), 31.70 (C-8), 32.01 (C-2)ⁱⁱⁱ, 32.10 (C-7)ⁱⁱⁱ, 32.76 (C-2′)ⁱⁱⁱ, 33.28 (C-4′)ⁱⁱⁱ, 36.70 (C-10), 37.43 (C-1), 38.38 (C-12), 41.70 (C-13), 42.84 (C-4), 49.90 (C-17), 50.50 (C-9), 56.24 (C-14), 65.42 (C-1′), 68.95 (C-7′), 72.63 (C-3), 72.87 (C-18), 82.95 (C-6′), 121.07 (C-6), 141.64 (C-5) ppm
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
¹³C NMR assignment qualifier iii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-2 / C-7; C-2′ / C-4′
Specific rotation	[αD] = −35.3 (c = 0.638, CHCl₃)
IR ṽ	3311 (m), 2933 (s), 2902 (s), 2854 (s), 1735 (m), 1583 (w), 1470 (m), 1463 (m), 1436 (m), 1380 (m), 1251 (m), 1190 (w), 1171 (w), 1093 (s), 1055 (m), 1007 (w), 960 (w), 940 (w), 888 (w), 871 (w), 805 (m), 775 (w) cm⁻¹

(3S,9S,10R,13S,14S,17S)-17-({2-[3-(But-3-yn-1-yl)-3H-diazirin-3-yl]ethoxy}methyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
Identifier	SPAP X, 26
¹H NMR (400 MHz, CDCl₃, the spectra contains traces of CH₂Cl₂ with a signal at δ = 5.31 ppm)	δ = 0.64 (s, 3H, C19-H3), 0.92 – 1.19 (m, 5H, C14-H, C9-H, C15-HA, C12-HA, C1-HA) superimposed by 1.01 (s, 3H, C20-H3), 1.27 – 1.33 (m, 1H, C16-HA), 1.43 – 1.52 (m, 3H, C8-H, C11-H2), 1.55 – 1.63 (m, 2H, C7-HA, C2′-HA), 1.63 – 1.72 (m, 5H, C2′-HB, C4′-H2, C17-H, C15-HB), 1.77 – 1.88 (m, 4H, C16-HB, C2-H2, C1-HB), 1.91 (mc, 1H, C12-HB), 1.94 – 2.05 (m, 1H, C7-HB) superimposed by 1.96 (t, ²J5′,7′ = 2.7 Hz, 1H, C7′-H) and 2.03 (dt, J4′,5′ = 7.9 Hz, ²J7′,5′ = 2.6 Hz, 2H, C5′-H2), 2.18 – 2.33 (m, 2H, C4-H2), 3.22 (t, J2′,1′ = 6.2 Hz, 2H, C1′-H2) partially superimposed by AB signal (δA = 3.24, δB = 3.43, JAB = 9.3 Hz, additional splitting: J17,A = 7.2 Hz, J17,B = 6.9 Hz, 2H, C17-H2), 3.52 (mc, 1H, C3-H), 5.35 (mc, 1H, C6-H) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 12.36 (C-19), 13.33 (C-5′), 19.44 (C-20), 20.84 (C-11), 24.72 (C-15), 26.00 (C-16), 27.00 (C-3′), 31.68 (C-2), 31.97 (C-7, C-8), 32.76 (C-4′), 33.27 (C-2′), 36.61 (C-10), 37.30 (C-1), 38.36 (C-12), 41.69 (C-13), 42.32 (C-4), 49.90 (C-17), 50.41 (C-9), 56.20 (C-14), 65.42 (C-1′), 68.95 (C-7′), 71.79 (C-3), 72.86 (C-18), 82.94 (C-6′), 121.62 (C-6), 140.83 (C-5) ppm
Specific rotation	[αD] = −28.1 (c = 0.662, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₅₄H₈₁N₄O₄ [2M+H]⁺: 849.6252; found: 849.6238
IR ṽ	3380 (m, br), 3310 (m), 2933 (s), 2902 (s), 2866 (s), 1732 (w), 1653 (w), 1584 (w), 1464 (m), 1448 (m), 1436 (m), 1376 (m), 1333 (m), 1244 (w), 1227 (w), 1191 (w), 1112 (m), 1052 (m), 954 (w), 841 (w), 800 (w), 634 (m, br) cm⁻¹

Hex-5-yn-1-yl (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
Identifier	SI-35
¹H NMR (400 MHz, CDCl₃)	δ = 0.68 (s, 3H, C18-H3), 0.77 (ddd, J11A,9 = 11.3 Hz, J8,9 = 11.3 Hz, J11B,9 = 4.3 Hz, 1H, C9-H), 0.94 (mc, 1H, C7-HA), 1.01 (s, 3H, C19-H3), 1.06 – 1.16 (m, 1H, C14-H), 1.19 – 1.47 (m, 7H, C1-HA, C12-HA, C6-H2, C8-H, C11-HA, C15-HA), 1.50 – 1.65 (m, 4H, C5-H, C11-HB, C3″-H2), 1.66 – 1.84 (m, 5H, C7-HB, C15-HB, C16-HA, C2′-H2), 1.96 (t, ⁴J4″,6″ = 2.6 Hz, 1H, C6″-H), 1.97 – 2.17 (m, 4H, C4-HA, C12-HB, C1-HB, C16-HB), 2.23 (td, J3″,4″ = 6.9 Hz, ⁴J6″,4″ = 2.6 Hz, 2H, C4″-H2) superimposed by (m, 1H, C4-HB), 2.28 – 2.43 (m, 3H, C2-H2, C17-H), 4.09 (mc, 2H, C1″-H2) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.49 (C-19), 13.60 (C-18), 18.10 (C-4″), 21.33 (C-11), 23.60 (C-16), 24.49 (C-15), 25.10 (C-3″), 27.85 (C-2″), 28.86 (C-6), 31.69 (C-7), 35.53 (C-8), 35.72 (C-10), 38.15 (C-2), 38.39 (C-12), 38.56 (C-1), 44.14 (C-13), 44.68 (C-4), 46.69 (C-5), 53.77 (C-9), 55.35 (C-17), 55.78 (C-14), 63.55 (C-1″), 68.70 (C-6″), 83.90 (C-5″), 174.09 (C-1′), 211.94 (C-3) ppm
Specific rotation	[αD] = +81.9 (c = 0.769, CHCl₃)
IR ṽ	3289 (m), 2932 (s), 2848 (m), 1714 (s), 1446 (m), 1407 (w), 1386 (w), 1349 (w), 1292 (w), 1273 (w), 1254 (w), 1233 (w), 1210 (w), 1186 (m), 1157 (m), 1129 (m), 1071 (w), 1058 (w), 1036 (w), 1002 (w), 638 (br.) cm⁻¹

Hex-5-yn-1-yl (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro[cyclopenta[a]phenanthrene-3,3′-diazirine]-17-carboxylate
Identifier	SPAP XI, 27
¹H NMR (400 MHz, CDCl₃)	δ = 0.12 (mc, J = 14.4 Hz, J = 4.0 Hz, J = 2.1 Hz, 1H, C4-HA), 0.34 (mc, J = 14.8 Hz, J = 4.0 Hz, J = 2.1 Hz, 1H, C2-HA), 0.67 (s, 3H, C18-H3), 0.82 (ddd, J11A,9 = 11.3 Hz, J8,9 = 11.3 Hz, J11B,9 = 4.3 Hz, 1H, C9-H), 0.87 (s, 3H, C19-H3), 0.88 – 1.02 (m, 1H, C6-HA)ⁱ, 1.07 – 1.15 (m, 1H, C14-H), 1.15 – 1.34 (m, 6H, C1-HA, C7-H2, C11-HA, C12-HA, C15-HA)ⁱ, 1.38 (mc, 1H, C8-H), 1.49 – 1.64 (m, 4H, C5-H, C11-HB, C3″-H2), 1.65 – 1.84 (m, 7H, C1-HB, C4-HB, C6-HB, C15-HB, C16-HA, C2″-H2)ⁱ, 1.92 – 2.04 (m, 3H, C2-HB, C12-HB, C6″-H), 2.11 (mc, 1H, C16-HB), 2.23 (td, J3″,4″ = 7.0 Hz, ⁴J6″,4″ = 2.7 Hz, 2H, C4″-H2), 2.34 (t, J16,17 = 9.4 Hz, 1H, C17-H), 4.09 (mc, 2H, C1″-H2) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C6-H2 / C7-H2
¹³C NMR (100 MHz, CDCl₃)	δ = 11.17 (C-19), 13.59 (C-18), 18.10 (C-4″), 21.01 (C-11), 23.58 (C-16), 24.47 (C-15), 25.07 (C-3″), 27.60 (C-2), 27.84 (C-3, C-2″), 28.40 (C-7)ⁱ, 31.71 (C-6)ⁱ, 34.47 (C-4), 35.60 (C-8), 35.65 (C-10), 36.34 (C-1), 38.45 (C-12), 44.14 (C-13), 44.58 (C-5), 53.96 (C-9), 55.38 (C-17), 55.93 (C-14), 63.53 (C-1″), 66.67 (C-5″), 83.92 (C-6″), 174.17 (C-1′) ppm
¹³C NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C6-H2 / C7-H2
Specific rotation	[αD] = +49.1 (c = 0.738, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₆H₃₉N₂O₂ [M+H]⁺: 411.3006; found: 411.2917
IR ṽ	3309 (m), 2932 (s), 2853 (s), 1729 (s), 1577 (m), 1472 (w), 1450 (m), 1386 (m), 1350 (m), 1292 (w), 1256 (w), 1240 (m), 1214 (m), 1181 (m), 1156 (s), 1059 (w), 1044 (w), 958 (w), 635 (w) cm⁻¹

But-3-yn-1-yl (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-3-oxohexadecahydro-1H-cyclopenta[a]phenanthrene-17-carboxylate
Identifier	SI-36
¹H NMR (400 MHz, CDCl₃)	δ = 0.69 (s, 3H, C18-H3), 0.77 (ddd, J11A,9 = 11.1 Hz, J8,9 = 11.1 Hz, J11B,9 = 3.8 Hz, 1H, C9-H), 0.94 (mc, 1H, C7-HA), 1.01 (s, 3H, C19-H3), 1.11 (mc, 1H, C14-H), 1.20 – 1.47 (m, 8H, C2-HA, C1-HA, C6-H2, C8-H, C11-HA, C12-HA, C15-HA), 1.48 – 1.55 (m, 1H, C5-HA), 1.56 – 1.65 (m, 1H, C11-HB), 1.65 – 1.76 (m, 2H, C7-HB, C15-HB), 1.81 (mc, 1H, C16-HA), 1.99 (t, ⁴J2″,4″ = 2.6 Hz, 1H, C6″-H), 2.00 – 2.17 (m, 3H, C1-HB, C16-HB, C4-HA), 2.22 – 2.44 (m, 4H, C2-HB, C4-HB, C12-HB, C17-H), 2.55 (td, J1″,2″ = 6.7 Hz, ⁴J4″,2″ = 2.7 Hz, 2H, C2″-H2), AB signal (δA = 4.12, δB = 4.26, JAB = 10.6 Hz, additional splitting A: J2″,1″A = 6.7 Hz, additional splitting B: J2″,1″B = 6.7 Hz, 2H, C1″-H2) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.48 (C-19), 13.55 (C-18), 19.15 (C-2″), 21.30 (C-11), 23.55 (C-16), 24.50 (C-15), 28.86 (C-6), 31.69 (C-7), 35.54 (C-8), 35.72 (C-10), 38.16 (C-2), 38.27 (C-12), 38.56 (C-1), 44.24 (C-13), 44.68 (C-4), 46.67 (C-5), 53.76 (C-9), 55.18 (C-17), 55.81 (C-14), 61.88 (C-1″), 69.80 (C-4″), 80.45 (C-3″), 173.83 (C-1′), 211.94 (C-3) ppm
Specific rotation	[αD] = +43.69 (c = 0.436, CHCl₃)
IR ṽ	3274 (m, br.), 2932 (s), 2860 (m), 1713 (s), 1472 (w), 1447 (m), 1417 (w), 1386 (m), 1351 (m), 1331 (w), 1292 (m), 1272, 1213 (m), 1190 (m), 1158 (s), 1117 (w), 1074 (w), 1055 (w), 1046 (w), 1008 (w), 953 (w), 774 (w), 735 (w), 691 (w), 646 (w) cm⁻¹

But-3-yn-1-yl (5S,8R,9S,10S,13S,14S,17S)-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro[cyclopenta[a]phenanthrene-3,3′-diazirine]-17-carboxylate
Identifier	SPAP XII, 28
¹H NMR (400 MHz, CDCl₃, the spectrum contains traces of CH₂Cl₂ with a signal at δ = 5.31 ppm)	δ = 0.12 (ddd, J = 14.4 Hz, J = 4.0 Hz, J = 2.1 Hz, 1H, C4-HA), 0.34 (ddt, J = 14.8 Hz, J = 4.7 Hz, J = 2.3 Hz, 1H, C2-HA), 0.68 (s, 3H, C18-H3), 0.82 (mc, 1H, C9-H), 0.87 (s, 3H, C19-H3), 0.95 (mc, 1H, C7-HA), 1.08 – 1.17 (m, 1H, C14-H), 1.18 – 1.35 (m, 6H, C1-HA, C6-H2, C11-HA, C12-HA, C15-HA), 1.39 (mc, 1H, C8-H), 1.50 – 1.63 (m, 2H, C5-H, C11-HB), 1.64 – 1.85 (m, 5H, C1-HB, C4-HB, C7-HB, C15-HB, C16-HA), 1.98 (t, ⁴J2″,4″ = 2.6 Hz, 1H, C4″-H) superimposed by (m, 1H, C2-HB), 2.03 – 2.17 (m, 2H, C12-HB, C16-HB), 2.37 (t, J16,17 = 9.4 Hz, 1H, C17-H), 2.53 (dt, J1″,2″ = 6.7 Hz, ⁴J4″,2″ = 2.7 Hz, 2H, C2″-H2), AB signal (δA = 4.12, δB = 4.26, JAB = 10.6 Hz, additional splitting A: t, J2″,A = 6.8 Hz, additional splitting B: t, J2″,B = 6.8 Hz, 2H, C1″-H2) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.18 (C-19), 13.55 (C-18), 19.15 (C-2″), 20.98 (C-11), 23.55 (C-15), 24.49 (C-16), 27.60 (C-2), 27.84 (C-3), 28.39 (C-6), 31.71 (C-7), 34.47 (C-4), 35.62 (C-8), 35.65 (C-10), 36.33 (C-1), 38.35 (C-12), 44.24 (C-13), 44.58 (C-5), 53.94 (C-9), 55.20 (C-17), 55.96 (C-14), 61.86 (C-1″), 69.80 (C-4″), 80.45 (C-3″), 173.90 (C-1′) ppm
Specific rotation	[αD] = +34.0 (c = 1.076, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₄H₃₄N₂O₂Na [M+Na]⁺: 405.2513; found: 405.2421
IR ṽ	3307 (m), 3298 (m), 3259 (m), 2929 (s), 2853 (s), 1730 (s), 1577 (m), 1470 (w), 1451 (m), 1386 (m), 1350 (w), 1292 (w), 1275 (w), 1256 (m), 1214 (m), 1181 (m), 1156 (s), 1059 (w), 1044 (w), 1004 (w), 957 (w), 768 (w), 734 (w), 696 (w), 643 (w) cm⁻¹

(5S,8R,9S,10S,13S,14S,17S)-N-(but-3-yn-1-yl)-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro[cyclopenta[a]phenanthrene-3,3′-diazirine]-17-carboxamide
Identifier	SPAP XIII, 29
¹H NMR (400 MHz, CDCl₃)	δ = 0.12 (mc, 1H, C4-HA), 0.33 (mc, 1H, C2-HA), 0.69 (s, 3H, C18-H3), 0.77 – 0.86 (m, 1H, C9-H), 0.87 (s, 3H, C19-H3), 0.90 – 1.00 (m, 1H, C7-HA), 1.06 – 1.17 (m, 1H, C14-H), 1.18 – 1.45 (m, 7H, C6-H2, C8-H, C1-HA, C12-HA, C15-HA, C11-HA)ⁱ, 1.50 – 1.64 (m, 2H, C11-HB, C5-H), 1.64 – 1.82 (m, 5H, C1-HB, C16-HA, C15-HB, C7-HB, C4-HB)ⁱ, 1.92 – 2.06 (m, 3H, C2-HB, C12-HB, C4′-H), 2.07 – 2.25 (m, 2H, C16-HB, C17-H)ⁱ, 2.40 (mc, 2H, C2′-H2), 3.31 (mc, 1H, C1′-HA), 3.52 (mc, 1H, C1′-HB), 5.62 (mc, 1H, C1′-NH) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.19 (C-19), 13.27 (C-18), 19.69 (C-2′), 21.06 (C-11), 23.43 (C-16)ⁱ, 24.45 (C-15)ⁱ, 27.60 (C-2), 27.84 (C-3), 28.38 (C-6), 31.72 (C-7), 34.46 (C-4), 35.54 (C-10)ⁱ, 35.67 (C-8)ⁱ, 36.36 (C-1), 37.91 (C-1′), 38.58 (C-12), 43.86 (C-13), 44.60 (C-5), 53.99 (C-9), 56.16 (C-14), 57.15 (C-17), 69.91 (C-4′), 81.99 (C-3′), 172.80 (C-20) ppm
NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C15-H2 / C16-H2; C-10 / C-8
Specific rotation	[αD] = +15.54 (c = 0.364, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₄H₃₅N₃ONa [M+Na]⁺: 404.2672; found: 404.2579
IR ṽ	3309 (br), 2929 (s), 2853 (s), 1730 (m), 1651 (m), 1577 (w), 1530 (m), 1470 (w), 1386 (m), 1364 (w), 1293 (w), 1257 (m), 1231 (w), 1180 (w), 1160 (w), 1068 (w), 1030 (w), 639 (w) cm⁻¹

(5S,8R,9S,10S,13S,14S,17S)-N-(hex-5-yn-1-yl)-10,13-dimethyl-1,2,4,5,6,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro[cyclopenta[a]phenanthrene-3,3′-diazirine]-17-carboxamide
Identifier	SPAP XIV, 30
¹H NMR (400 MHz, CDCl₃)	δ = 0.12 (mc, 1H, C4-HA), 0.33 (mc, 1H, C2-HA), 0.68 (s, 3H, C18-H3), 0.81 (ddd, J11A,9 = 11.1 Hz, J8,9 = 11.1 Hz, J10B,9 = 3.9 Hz, 1H, C9-H), 0.87 (s, 3H, C19-H3), 0.94 (mc, 1H, C7-HA), 1.05 – 1.17 (m, 1H, C14-H), 1.18 – 1.45 (m, 8H, C6-H2, C3′-H, C12-HA, C15-HA, C1-HA, C11-HA, C8-H)ⁱ, 1.49 – 1.82 (m, 10H, C3′-HB, C4-HA, C2′-H2, C5-H, C11-HB, C7-HB, C16-HA, C15-HB, C1-HB)ⁱ, 1.88 – 2.03 (m, 3H, C12-HB, C6′-H, C2-HB), 2.04 – 2.11 (m, 1H, C17-H), 2.12 – 2.19 (m, 1H, C16-HB)ⁱ, 2.22 (td, J4″,3″ = 6.7 Hz; ⁴J4″,6″ = 2.6 Hz, 2H, C4′-H2), AB signal (δA = 3.22, δB = 3.35, JAB = 13.2 Hz, additional splitting A: td, JA,2″ = 6.6 Hz, JA,NH = 6.6 Hz, additional splitting B: JB,2″ = 6.4 Hz, JB,NH = 6.4 Hz, 2H, C1′-H2), 5.31 (mc, 1H, C1′-NH) ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 11.19 (C-19), 13.33 (C-18), 18.11 (C-4′), 21.06 (C-11), 23.58 (C-16)ⁱ, 24.44 (C-15)ⁱ, 25.80 (C-2′), 27.60 (C-2), 27.84 (C-3), 28.37 (C-6), 29.01 (C-3′), 31.71 (C-7), 34.46 (C-4), 35.53 (C-8)ⁱ, 35.67 (C-10)ⁱ, 36.35 (C-1), 38.77 (C-1′), 38.85 (C-1), 43.83 (C-13), 44.60 (C-5), 53.99 (C-9), 56.12 (C-14), 57.29 (C-17), 68.67 (C-6′), 84.09 (C-5′), 172.70 (C-20) ppm
NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C15-H2 / C16-H2; C-8 / C-10
Specific rotation	[αD] = +38.86 (c = 0.615, CHCl₃)
HRMS m/z (pos. ESI+)	Calcd. for C₂₆H₄₀N₃O [M+H]⁺: 410.3166; found: 410.3086
IR ṽ	3308 (br.), 2929 (s), 2853 (s), 1730 (m), 1647 (m), 1576 (w), 1531 (s), 1471 (w), 1449 (m), 1386 (w), 1365 (w), 1293 (w), 1257 (w), 1230 (w), 1181 (w), 1158 (w), 633 (w) cm⁻¹

Methyl (R)-4-[(3R,5R,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-39
¹H NMR (400 MHz, CDCl₃, the spectrum contains traces of CH₂Cl₂ and EtOAc with signals at δ = 1.26, 2.04, 4.12 and 5.31 ppm)	δ = 0.65 (s, 3H, C18-H3), 0.84 (s, 3H, C19-H3), 0.85 – 0.94 (m, 1H, C9-H) superimposed by 0.92 (d, J4′,5′ = 6.3 Hz, 3H, C5′-H3), 0.99 – 1.18 (m, 4H, C1-H2, C2-H2)ⁱⁱ, 1.22 – 1.35 (m, 5H, C8-H, C11-H2, C12-H2)ⁱⁱ, 1.38 – 1.47 (m, 1H, C14-H)ⁱⁱ, 1.47 – 1.59 (m, 2H, C15-H2)ⁱⁱ, 1.70 – 1.93 (m, 7H, C16-H2, C17-H, C3′-H2, C2′-H2)ⁱⁱ, 1.99 – 2.06 (m, 1H, C4′-H)ⁱⁱ, 2.09 – 2.27 (m, 4H, C7-H2, C4-HB, C5-H)ⁱⁱ, 2.35 (ddd, ²J4B,4A = 15.3 Hz, J3,4A = 10.1 Hz, J5,4A = 5.3 Hz, 1H, C4-HA)ⁱ, 3.66 (s, 3H, C1′-OCH3) superimposed by (mc, 1H, C3-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment of the coupling constants between 4-CH2 / 3-H and 4-CH2 / 5-H is not possible
¹H NMR assignment qualifier ii	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable

Methyl (R)-4-[(3R,5S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-40
¹H NMR (400 MHz, CDCl₃)	δ = 0.66 (s, 3H, C18-H3), 0.72 (s, 3H, C19-H3), 0.92 (d, J4′,5′ = 6.4 Hz, 3H, C5′-H3), 1.00 – 1.19 (m, 2H, C1-H2)ⁱ, 1.20 – 1.37 (m, 6H, C2-H2, C11-H2, C12-H2)ⁱ, 1.38 – 1.59 (m, 4H, C8-H, C9-H, C15-H2)ⁱ,ⁱⁱ, 1.60 – 1.67 (m, 3H, C14-H, C16-H2)ⁱ, 1.68 – 1.72 (m, 2H, C3′-H2), 1.74 – 1.84 (m, 2H, C2′-H2), 1.83 – 1.93 (m, 1H, C4′-H), 1.97 – 2.05 (m, 2H, C7-H2)ⁱ, 2.16 – 2.40 (m, 3H, C4-H2, C17-H), 2.71 (mc, 1H, C5-H), 3.66 (s, 3H, C1′-OCH3), 4.16 (br. m, 1H, C3-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable
¹H NMR assignment qualifier ii	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement

Methyl (R)-4-[(3R,5S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-3-[(methylsulfonyl)oxy]-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-41
¹H NMR (400 MHz, CDCl₃, the spectra contains traces of CH₂Cl₂ with a signal at δ = 5.31 ppm)	δ = 0.66 (s, 3H, C19-H3), 0.73 (s, 3H, C18-H3), 0.92 (d, J4′,5′ = 6.4 Hz, 3H, C5′-H3), 1.06 – 1.44 (m, 10H, C1-H2, C2-H2, C11-H2, C12-H2, C15-H2)ⁱ, 1.50 – 1.73 (m, 4H, C8-H, C9-H, C14-H, C16-HA)ⁱ,ⁱⁱ, 1.73 – 1.85 (m, 3H, C4′-H, C7-H2)ⁱ, 1.84 – 1.93 (m, 1H, C16-HB)ⁱ, 1.94 – 2.03 (m, 4H, C2′-H2, C3′-H2)ⁱ, 3.22 (ddd, ²J4B,4A = 15.7 Hz, J5,4A = 9.6 Hz, J3,4A = 6.6 Hz, 1H, C4-HA)ⁱ, 2.28 – 2.39 (m, 2H, C4-HB, C17-H)ⁱ, 2.62 (dd, J4A,5 = 9.6 Hz, J4B,5 = 3.5 Hz, 1H, C5-H), 2.99 [s, 3H, C3-OS(O2)CH3], 3.66 (s, 3H, C1′-OCH3), 5.04 (mc, 1H, C3-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable
¹H NMR assignment qualifier ii	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement

Methyl (R)-4-[(3S,5S,8S,9S,10R,13R,14S,17R)-3-acetoxy-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoate
Identifier	SI-42
¹H NMR (400 MHz, CDCl₃)	δ = 0.66 (s, 3H, C18-H3), 0.76 (s, 3H, C19-H3), 0.92 (d, J4′,5′ = 6.4 Hz, 3H, C5′-H3), 1.02 – 1.19 (m, 2H, C1-H2)ⁱ, 1.20 – 1.39 (m, 7H, C2-H2, C7-H2, C8-H, C11-H2)ⁱ, 1.39 – 1.50 (m, 1H, C9-H)ⁱ, 1.50 – 1.65 (m, 4H, C12-H2, C15-H2)ⁱ, 1.72 – 1.95 (m, 6H, C16-H2, C17-H, C4′-H, C3′-H2)ⁱ, 1.98 – 2.05 (m, 1H, C14-H)ⁱ superimposed by 2.02 (s, 3H, C21-H3), 2.17 – 2.40 (m, 4H, C4-H2, C2′-H2)ⁱ, 3.66 (s, 3H, C1′-OCH3), 4.67 (mc, 1H, C3-H) ppm
¹H NMR assignment qualifier i	Unequivocal assignment not possible. The assignment of all marked protons is interchangeable

(R)-4-[(3S,5S,8S,9S,10R,13R,14S,17R)-3-Hydroxy-10,13-dimethyl-6-oxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
Identifier	SI-43
¹H NMR (400 MHz, CDCl₃, the spectra contains traces of MeOH with a signal at δ = 3.50 ppm)	δ = 0.67 (s, 3H, C18-H3), 0.76 (s, 3H, C19-H3), 0.93 (d, J4′,5′ = 6.5 Hz, 3H, C5′-H3), 1.03 – 1.19 (m, 2H, C8-H, C9-H)ⁱ, 1.19 – 1.29 (m, 3H, C1-H2, C2-HA)ⁱ, 1.29 – 1.39 (m, 2H, C2-HB, C7-HA)ⁱ, 1.40 – 1.67 (m, 8H, C7-HB, C11-H2, C12-H2, C14-H, C15-H2)ⁱ, 1.73 – 1.99 (m, 6H, C16-H2, C4′-H, C17-H, C3′-H2)ⁱ, 1.99 – 2.06 (mc, 1H, C2′-HA)ⁱ, 2.17 – 2.35 (m, 3H, C2′-HB, C5-H, C4-HA)ⁱ, 2.41 (ddd, ²J4A,4B = 15.5 Hz, J3,4B = 10.1 Hz, J5,4B = 6.5 Hz, 1H, C4-HB)ⁱ, 3.58 (mc, 1H, C3-H) ppm

Hex-5-yn-1-yl (R)-4-[(3S,5S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-1,2,3,4,5,7,8,9,10,11,12,13,14,15,16,17-hexadecahydrospiro(cyclopenta[a]phenanthrene-6,3′-diazirin)-17-yl]pentanoate
Identifier	Trans-sterol, 1
¹H NMR (400 MHz, CDCl₃, the spectrum contains an unknown impurity with a signal at δ = 3.65 ppm, that is also found in the ¹H NMR spectrum in the literature)	δ = 0.36 – 0.48 (m, 2H, C7-HA, C4-HA), 0.68 (s, 3H, C18-H3), 0.72 – 0.83 (m, 2H, C9-H, C4-HB), 0.91 (d, J4′,5′ = 6.5 Hz, C5′-H3), 0.93 – 1.20 (m, 5H, C17-H, C15-HA, C14-H, C1-HA, C12-HA) superimposed by 1.12 (s, 3H, C10-H3), 1.20 – 1.47 (m, 7H, C3′-HA, C4′-H, C16-HA, C15-HB, C7-HB, C2-HA, C11-HA), 1.48 – 1.67 (m, 3H, C3″-H2, C11-HB)ⁱ, 1.65 – 1.88 (m, 8H, C2′-H2, C3′-HB, C16-HB, C8-H, C5-H, C2-HB, C1-HB), 1.95 (t, ⁴J4″,6″ = 2.6 Hz, 1H, C6″-H), 2.00 (dt, ²J12A,12,B = 12.8 Hz, 1H, C12-HB), 2.15 – 2.24 (m, 1H, C1′-HA) superimposed by 2.22 (td, J3′,4′ = 7.1 Hz, ⁴J6″,4″ = 2.6 Hz, 2H, C4″-H2), 2.33 (ddd, ²J1′A,1′B = 15.2 Hz, J2′A,1′B = 10.0 Hz, J2′B,1′B = 5.2 Hz, 1H, C1′-HB), 3.45 (mc, 1H, C3-H), 4.07 (t, J2″,1″ = 6.4 Hz, 2H, C1″-H2) ppm
¹H NMR assignment qualifier i	Superimposed by the signal from traces of H₂O (δ = 1.56 ppm) in the CDCl₃ used for this measurement
¹⁵N NMR (41 MHz, CDCl₃)	δ = 73.02 (C6-Nax=Neq)ⁱⁱⁱ, 73.41 (C6-Nax=Neq)ⁱⁱⁱ ppm
¹³C NMR (100 MHz, CDCl₃)	δ = 12.06 (C-18), 12.98 (C-19), 18.09 (C-4″), 18.24 (C-5″), 21.20 (C-11), 23.87 (C-15), 24.96 (C-3″), 27.71 (C-2″), 27.96 (C-16), 29.33 (C-6), 30.67 (C-2), 30.94 (C-3′), 31.25 (C-2′), 33.14 (C-4), 33.84 (C-8), 35.30 (C-4′), 36.32 (C-1)ⁱⁱ, 37.32 (C-7), 37.54 (C-10), 39.69 (C-12), 42.72 (C-13), 45.25 (C-5), 53.66 (C-9), 55.81 (C-17)ⁱⁱⁱ, 55.98 (C-14)ⁱⁱⁱ, 63.75 (C-1″), 68.71 (C-6″), 71.03 (C-3), 83.87 (C-5″), 174.29 (C-1′) ppm
¹³C NMR assignment qualifier ii	The assignment of this signal was possible through comparison with the NMR analysis of structurally similar compounds. The respective signal was unequivocally assigned through 2D NMR data in the analysis of the ladder and due to structural resemblance, the same assignment was made in this analysis
NMR assignment qualifier iii	Unequivocal assignment not possible. The assignment of the following nuclei is interchangeable: C-14 / C-17; 6-Nax / 6-Neq
HRMS m/z (pos. ESI+)	Calcd. for C₃₀H₅₀N₃O₃ [M+NH₄]⁺: 500.3846; found: 500.3776
IR ṽ	3491 (br, m), 3309 (m), 2935 (s), 2867 (s), 2849 (s), 1732 (s), 1583 (m), 1561 (w), 1468 (m), 1444 (m), 1380 (m), 1361 (m), 1329 (m), 1308 (m), 1270 (m), 1249 (s), 1221 (m), 1165 (s), 1098 (w), 1052 (w), 962 (w), 636 (br, m) cm⁻¹

NMR spectra
Spectrum images	Image data were not transcribed