Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester

Base Information

• Chemical Name: Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester
• CAS No.: 400643-69-8
• Molecular Formula: C₄₇H₇₀O₄Si
• Molecular Weight: 727.156
• Mol file: 400643-69-8.mol

Synonyms:Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester

Chemical Property of Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester

There total 15 articles about Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl 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: 80.0%

Acetic acid (R)-4-methyl-3-(2-oxo-ethyl)-pentyl ester (400643-62-1) + (Z)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17-(20)-ene (400643-61-0) → Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester (400643-69-8) + Acetic acid (3R,5S,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester (400643-68-7)

Guidance literature:

With dimethylaluminum chloride; In dichloromethane; at -78 - -30 ℃; for 6h;

DOI:10.1016/S0040-4039(01)01964-5

Reference yield: 56.0%

Acetic acid (3R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-isopropyl-5-oxo-heptyl ester (400643-72-3) → Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester (400643-69-8) + Acetic acid (3R,5S,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester (400643-68-7)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol;

DOI:10.1016/S0040-4039(01)01964-5

Reference yield:

D-limonene (5989-27-5,555-08-8,8022-90-0,9003-73-0,95327-98-3) → Acetic acid (3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5-hydroxy-3-isopropyl-heptyl ester (400643-69-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: H₂ / PtO₂ / methanol

2.1: O₃ / CH₂Cl₂; methanol / 1 h / -60 °C

2.2: p-TsOH / methanol / 1 h / -60 - 0 °C

3.1: 100 percent / HClO₄ / H₂O; tetrahydrofuran

4.1: 98 percent / lithium tris[(3-ethyl-3-pentyl)oxy]aluminohydride / tetrahydrofuran / 1 h / -78 °C

5.1: 96 percent / DBU / CH₂Cl₂

6.1: 100 percent / MCPBA / CHCl₃ / 48 h / Heating

7.1: 60 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

8.1: 66 percent / pyridinium dichromate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h

9.1: <2.0 equiv. Me₂AlCl / CH₂Cl₂

10.1: 56 percent / NaBH₄ / ethanol; tetrahydrofuran

With sodium tetrahydroborate; dipyridinium dichromate; perchloric acid; Lithium tris[(3-ethyl-3-pentyl)-oxy]aluminohydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; dimethylaluminum chloride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; 6.1: Baeyer-Villiger reaction / 9.1: Oppenhauer-like oxidation;

DOI:10.1016/S0040-4039(01)01964-5

upstream raw materials:

Acetic acid (R)-4-methyl-3-(2-oxo-ethyl)-pentyl ester

(Z)-3β-[(tert-butyldiphenylsilyl)oxy]-5α-pregn-17-(20)-ene

Acetic acid (3R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S)-3-(tert-butyl-diphenyl-silanyloxy)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-3-isopropyl-5-oxo-heptyl ester

Epiandrosterone

Downstream raw materials:

(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-ol

(4S,6R)-6-{(S)-1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-ethyl}-4-isopropyl-tetrahydro-pyran-2-one

(3R,5R,6S)-6-[(3S,5S,8R,9S,10S,13S,14S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-3-isopropyl-heptane-1,5-diol