(S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

Base Information

• Chemical Name: (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester
• CAS No.: 135716-15-3
• Molecular Formula: C₃₉H₆₀O₆Si
• Molecular Weight: 652.987
• Mol file: 135716-15-3.mol

Synonyms:

Chemical Property of (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

There total 5 articles about (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-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:

pravastatin lactone (85956-22-5) → (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester (135716-15-3)

Guidance literature:

Multi-step reaction with 5 steps

1: DMAP, imidazole / tetrahydrofuran

2: H₂ / 10percent Pt-C / ethyl acetate

3: 86 percent / 48percent aq. HF / acetonitrile

4: 1) DiBAL, 2) NaBH₄ / 1) PhMe-THF, -78 deg C, 2) MeOH-THF

5: imidazole / dimethylformamide

With 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; platinum on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

pravastatin (81093-37-0,81131-74-0,250737-12-3) → (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester (135716-15-3)

Guidance literature:

Multi-step reaction with 6 steps

1: CF₃CO₂H

2: DMAP, imidazole / tetrahydrofuran

3: H₂ / 10percent Pt-C / ethyl acetate

4: 86 percent / 48percent aq. HF / acetonitrile

5: 1) DiBAL, 2) NaBH₄ / 1) PhMe-THF, -78 deg C, 2) MeOH-THF

6: imidazole / dimethylformamide

With 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; trifluoroacetic acid; platinum on activated charcoal; In tetrahydrofuran; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

Reference yield:

(S)-2-Methyl-butyric acid (1S,3S,7S,8S,8aR)-3-(tert-butyl-dimethyl-silanyloxy)-8-[2-((2R,4R)-4-hydroxy-6-oxo-tetrahydro-pyran-2-yl)-ethyl]-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester (133805-99-9) → (S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-[(3R,5S)-7-(tert-butyl-diphenyl-silanyloxy)-3,5-dihydroxy-heptyl]-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester (135716-15-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10percent Pt-C / ethyl acetate

2: 86 percent / 48percent aq. HF / acetonitrile

3: 1) DiBAL, 2) NaBH₄ / 1) PhMe-THF, -78 deg C, 2) MeOH-THF

4: imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; platinum on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/0040-4039(91)80587-V

upstream raw materials:

(S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-3-hydroxy-7-methyl-8-((3R,5S)-3,5,7-trihydroxy-heptyl)-decahydro-naphthalen-1-yl ester

tert-butylchlorodiphenylsilane

pravastatin

pravastatin lactone

Downstream raw materials:

(S)-2-Methyl-butyric acid (1S,4aS,7S,8S,8aS)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3-oxo-decahydro-naphthalen-1-yl ester

(S)-2-Methyl-butyric acid (1S,3R,4aS,7S,8S,8aS)-8-(2-{(4R,6S)-6-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-3-hydroxy-7-methyl-decahydro-naphthalen-1-yl ester

Refernces