Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Base Information

• Chemical Name: Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester
• CAS No.: 865441-04-9
• Molecular Formula: C₃₉H₅₂O₄Si
• Molecular Weight: 612.925

Synonyms:

Chemical Property of Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester

There total 7 articles about Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-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: 84.0%

tert-Butyl-[(3S,8R,9S,10R,13S,14S,15S,16R)-17-eth-(E)-ylidene-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[15,16]cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane (865441-03-8) + acetic acid (64-19-7,77671-22-8) → Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (865441-04-9)

Guidance literature:

With titanium(IV) isopropylate;

DOI:10.1016/j.tetlet.2005.07.042

Reference yield:

(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-17-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthrene → Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (865441-04-9)

Guidance literature:

Multi-step reaction with 4 steps

1: O₂ / Pd(OAc)2

2: 83 percent / TBHP; Triton B

3: 83 percent / KHMDS

4: 84 percent / Ti(OiPr)4

With titanium(IV) isopropylate; tert.-butylhydroperoxide; oxygen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; palladium diacetate; 3: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.042

Reference yield:

dehydroepiandrosterone (53-43-0) → Acetic acid (3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-butyl-diphenyl-silanyloxy)-17-eth-(E)-ylidene-15-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester (865441-04-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / Im

2: LDA

3: O₂ / Pd(OAc)2

4: 83 percent / TBHP; Triton B

5: 83 percent / KHMDS

6: 84 percent / Ti(OiPr)4

With titanium(IV) isopropylate; tert.-butylhydroperoxide; impramine; oxygen; N-benzyl-trimethylammonium hydroxide; potassium hexamethylsilazane; lithium diisopropyl amide; palladium diacetate; 5: Wittig reaction;

DOI:10.1016/j.tetlet.2005.07.042

upstream raw materials:

tert-Butyl-[(3S,8R,9S,10R,13S,14S,15S,16R)-17-eth-(E)-ylidene-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-20-oxa-cyclopropa[15,16]cyclopenta[a]phenanthren-3-yloxy]-diphenyl-silane

acetic acid

(3S,8R,9S,10R,13S,14S)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14-dodecahydro-cyclopenta[a]phenanthren-17-one

(3S,8R,9S,10R,13S,14S,15S,16S)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-20-oxa-cyclopropa[15,16]cyclopenta[a]phenanthren-17-one

Downstream raw materials:

(3S,8R,9S,10R,13R,14S,15R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-17-((1R,3R)-3-hydroxy-1,5-dimethyl-hexyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-15-ol

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

(R)-3-[(3S,8R,9S,10R,13R,14S,15R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-15-triethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butyraldehyde

(R)-3-[(3S,8R,9S,10R,13R,14S,15R,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-10,13-dimethyl-15-triethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-butyric acid ethyl ester

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