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

Base Information

• Chemical Name: 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
• CAS No.: 865441-03-8
• Molecular Formula: C₃₇H₄₈O₂Si
• Molecular Weight: 552.872

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 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

There total 6 articles about 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 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: 83.0%

(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 (865441-02-7) + ethyltriphenylphosphonium iodide (4736-60-1) → 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)

Guidance literature:

With potassium hexamethylsilazane;

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 → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: O₂ / Pd(OAc)2

2: 83 percent / TBHP; Triton B

3: 83 percent / KHMDS

With 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) → 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)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / Im

2: LDA

3: O₂ / Pd(OAc)2

4: 83 percent / TBHP; Triton B

5: 83 percent / KHMDS

With 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:

(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

ethyltriphenylphosphonium iodide

(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

dehydroepiandrosterone

Downstream raw materials:

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

C₅₇H₇₂O₅Si

(2R,4S)-2-[(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]-6-methyl-heptan-4-ol

(2R,4R)-2-[(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]-6-methyl-heptan-4-ol

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