Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Base Information

Chemical Name:Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester
CAS No.:335197-18-7
Molecular Formula:C₄₁H₆₈O₄Si
Molecular Weight:653.074
Hs Code.:

Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Synonyms:Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

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Chemical Property of Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

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Technology Process of Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

There total 11 articles about Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-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:

: 75-36-5
acetyl chloride

: (3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-16-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene

: 335197-18-7
Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Guidance literature:: (3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-16-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.166667h;

acetyl chloride; In tetrahydrofuran; at -30 - 25 ℃; Further stages.;
DOI:10.1021/ja004098t

Reference yield:

: 53-43-0
dehydroepiandrosterone

: 335197-18-7
Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / SeO₂; t-BuOOH / CH₂Cl₂ / 5 h / 0 °C

2.1: 96 percent / oxalyl chloride; DMSO / CH₂Cl₂ / -50 - 25 °C

3.1: tert-BuLi; CuCN; LiCl / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C

3.2: tetrahydrofuran / -78 - 25 °C

4.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

4.2: tetrahydrofuran / -30 - 25 °C

With tert.-butylhydroperoxide; selenium(IV) oxide; oxalyl dichloride; potassium tert-butylate; tert.-butyl lithium; dimethyl sulfoxide; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 4.1: Swern oxidation;
DOI:10.1021/ja012119t

Reference yield:

: 68877-57-6
Cyclohexyl ethynyl ether

: 335197-18-7
Acetic acid (3S,8R,9S,10R,13S,14S)-3-(tert-butyl-dimethyl-silanyloxy)-17-((Z)-(S)-2-cyclohexyloxy-1,5-dimethyl-hex-2-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-BuLi / tetrahydrofuran / 0.33 h / 0 °C

1.2: 85 percent / tetrahydrofuran / 10 h / 25 °C

2.1: 99 percent / TMSBr; MeOH / CH₂Cl₂ / -20 - 20 °C

3.1: tert-BuLi; CuCN; LiCl / diethyl ether; tetrahydrofuran / 0.75 h / -78 °C

3.2: tetrahydrofuran / -78 - 25 °C

4.1: t-BuOK / tetrahydrofuran / 0.17 h / 0 °C

4.2: tetrahydrofuran / -30 - 25 °C

With methanol; n-butyllithium; trimethylsilyl bromide; potassium tert-butylate; tert.-butyl lithium; lithium chloride; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/ja012119t