Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Base Information

• Chemical Name: Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester
• CAS No.: 442631-46-1
• Molecular Formula: C₄₈H₆₂O₅S₂Si
• Molecular Weight: 811.235

Synonyms:Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Chemical Property of Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

Chemical Property:

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Technology Process of Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester

There total 5 articles about Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

dibenzyl peroxydicarbonate (2144-45-8) + [bis(phenylthio)methyl]lithium (13307-76-1) + (3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-eth-(E)-ylidene-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one (505093-51-6) → Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (442631-46-1)

Guidance literature:

[bis(phenylthio)methyl]lithium; (3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-eth-(E)-ylidene-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one;

With N,N,N,N,N,N-hexamethylphosphoric triamide; at 25 ℃; for 2h;

dibenzyl peroxydicarbonate; at -78 ℃; for 0.0833333h; Further stages.;

DOI:10.1021/ja012119t

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (442631-46-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 99 percent / Et₃N / CH₂Cl₂ / 12 h / 25 °C

2.1: 73 percent / H₂NNH₂*H₂O / tetrahydrofuran; methanol / 8 h / Heating

3.1: 96 percent / Dess-Martin periodinane

4.2: HMPA / 2 h / 25 °C

4.3: 63 percent / 0.08 h / -78 °C

With Dess-Martin periodane; hydrazine hydrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja012119t

Reference yield:

3β-{[tert-butyl(dimethyl)silyl]oxy}-16α,17α-epoxypregn-5-en-20-one (285554-48-5) → Carbonic acid benzyl ester (3S,8R,9S,10R,13S,14S,17S)-3-(tert-butyl-dimethyl-silanyloxy)-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-16-oxo-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (442631-46-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 73 percent / H₂NNH₂*H₂O / tetrahydrofuran; methanol / 8 h / Heating

2.1: 96 percent / Dess-Martin periodinane

3.2: HMPA / 2 h / 25 °C

3.3: 63 percent / 0.08 h / -78 °C

With Dess-Martin periodane; hydrazine hydrate; In tetrahydrofuran; methanol;

DOI:10.1021/ja012119t

upstream raw materials:

dibenzyl peroxydicarbonate

[bis(phenylthio)methyl]lithium

(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-eth-(E)-ylidene-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one

tert-butyldimethylsilyl chloride

Downstream raw materials:

(3S,8R,9S,10R,13S,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-hydroxy-10,13-dimethyl-17-(1-methyl-2,2-bis-phenylsulfanyl-ethyl)-1,2,3,4,7,8,9,10,11,12,13,14,15,17-tetradecahydro-cyclopenta[a]phenanthren-16-one

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