(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

Base Information

• Chemical Name: (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
• CAS No.: 136491-73-1
• Molecular Formula: C₄₂H₆₂O₆Si
• Molecular Weight: 691.036

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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,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 (136491-73-1)

Guidance literature:

Multi-step reaction with 7 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

6: p-TsOH

7: Dess-Martin periodinane / CH₂Cl₂; 2-methyl-propan-2-ol

With 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

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,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 (136491-73-1)

Guidance literature:

Multi-step reaction with 8 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

7: p-TsOH

8: Dess-Martin periodinane / CH₂Cl₂; 2-methyl-propan-2-ol

With 1H-imidazole; dmap; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; trifluoroacetic acid; platinum on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

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,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 (136491-73-1)

Guidance literature:

Multi-step reaction with 6 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

5: p-TsOH

6: Dess-Martin periodinane / CH₂Cl₂; 2-methyl-propan-2-ol

With 1H-imidazole; sodium tetrahydroborate; hydrogen fluoride; hydrogen; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; platinum on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol;

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

upstream raw materials:

(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

pravastatin

pravastatin lactone

(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

Downstream raw materials:

(4aR,5S,6S,8aS)-5-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-6-methyl-4a,5,6,7,8,8a-hexahydro-1H-naphthalen-2-one

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