Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester

Base Information

• Chemical Name: Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester
• CAS No.: 151534-52-0
• Molecular Formula: C₄₅H₆₄O₆Si
• Molecular Weight: 729.085

Synonyms:

Chemical Property of Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester

There total 6 articles about Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-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:

1-bromo-4-methylpent-3-ene (2270-59-9) → Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester (151534-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Mg / 1) Et₂O, a) r.t., 0.5 h, b) reflux, 2-3 h, 2) Et₂O, r.t., 1 h

2: pyridine / 72 h / Ambient temperature

3: 82 percent / tert-butyl hydroperoxide, VO(AcAc)2 / CH₂Cl₂ / 24 h / Ambient temperature

4: 1) BH₃*DMS, 2) PCC, silica gel / 1) CH₂Cl₂, r.t., 24 h, 2) CH₂Cl₂, 2 h, ultrasounds

With pyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; silica gel; magnesium; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81873-1

Reference yield:

(3S,8S,9S,10R,13S,14S,16S,17R)-3-(tert-Butyl-diphenyl-silanyloxy)-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-ol (151534-44-0) → Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester (151534-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / 72 h / Ambient temperature

2: 82 percent / tert-butyl hydroperoxide, VO(AcAc)2 / CH₂Cl₂ / 24 h / Ambient temperature

3: 1) BH₃*DMS, 2) PCC, silica gel / 1) CH₂Cl₂, r.t., 24 h, 2) CH₂Cl₂, 2 h, ultrasounds

With pyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; silica gel; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81873-1

Reference yield:

(S)-5-Acetoxy-4-methyl-pentanoic acid (3S,8S,9S,10R,13S,14S,16S,17R)-17-acetyl-3-(tert-butyl-diphenyl-silanyloxy)-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 (151534-42-8) → Acetic acid (3S,5S,8R,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-10,13-dimethyl-6-oxo-hexadecahydro-cyclopenta[a]phenanthren-16-yl ester (151534-52-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Mg / 1) Et₂O, a) r.t., 0.5 h, b) reflux, 2-3 h, 2) Et₂O, r.t., 1 h

2: pyridine / 72 h / Ambient temperature

3: 82 percent / tert-butyl hydroperoxide, VO(AcAc)2 / CH₂Cl₂ / 24 h / Ambient temperature

4: 1) BH₃*DMS, 2) PCC, silica gel / 1) CH₂Cl₂, r.t., 24 h, 2) CH₂Cl₂, 2 h, ultrasounds

With pyridine; tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; dimethylsulfide borane complex; silica gel; magnesium; pyridinium chlorochromate; In dichloromethane;

DOI:10.1016/S0040-4020(01)81873-1

upstream raw materials:

C₄₅H₆₄O₅Si

1-bromo-4-methylpent-3-ene

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

Acetic acid (3S,8S,9S,10R,13S,14S,16S,17R)-3-(tert-butyl-diphenyl-silanyloxy)-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-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

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