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

Base Information

• Chemical Name: (7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one
• CAS No.: 116996-38-4
• Molecular Formula: C₃₇H₅₀O₄Si
• Molecular Weight: 586.887
• Mol file: 116996-38-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one 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: 93.0%

(7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-1,2,3,7,8,8a-hexahydro-naphthalen-1-ol (116996-37-3,117065-48-2) → (7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (116996-38-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.25h;

DOI:10.1021/ja00164a024

Reference yield:

4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde (116996-35-1,117065-46-0) → (7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (116996-38-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / C₈K, TiCl₃ / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h

2: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H₂O, MeCN, r.t., 1.75 h; 2.) CH₂Cl₂, 0 deg C, 40 min

3: 1.) (COCl)2; 2.Et₃N / 1.) DMSO, CH₂Cl₂, -78 deg C, 15 min; 2.) -78 deg C, 5 min

With titanium(III) chloride; oxalyl dichloride; 2-Methoxypropene; hydrogen fluoride; triethylamine; pyridinium p-toluenesulfonate; In 1,2-dimethoxyethane;

DOI:10.1021/ja00228a067

Reference yield:

<4R-<4α*(1R*,2S*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal (116996-31-7,126060-10-4) → (7S,8S,8aR)-8-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-7-methyl-3,7,8,8a-tetrahydro-2H-naphthalen-1-one (116996-38-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 50 percent / (Ph₃P)3RhCl / toluene; acetonitrile / 2.5 h / Heating

2: 1.) LDA / 1.) Et₂O, -78 deg C, 1 h; 2.) -78 deg C, 10 min

3: 96 percent / i-Pr₂NH / DMAP / diethyl ether / 36 h / Ambient temperature

4: 1.) O₃; 2.) Ph₃P / 1.) CH₂Cl₂, -78 deg C; 2.) -78 deg C, 20 min, r.t., 8 h

5: 85 percent / C₈K, TiCl₃ / 1,2-dimethoxy-ethane / r.t., 5 h; reflux, 3 h

6: 1.) HF; 2.) 2-methoxypropene / 2.) pyridinium p-toluenesulfonate / 1.) H₂O, MeCN, r.t., 1.75 h; 2.) CH₂Cl₂, 0 deg C, 40 min

7: 1.) (COCl)2; 2.Et₃N / 1.) DMSO, CH₂Cl₂, -78 deg C, 15 min; 2.) -78 deg C, 5 min

With Wilkinson's catalyst; titanium(III) chloride; oxalyl dichloride; 2-Methoxypropene; hydrogen fluoride; ozone; triethylamine; diisopropylamine; triphenylphosphine; lithium diisopropyl amide; dmap; pyridinium p-toluenesulfonate; In 1,2-dimethoxyethane; diethyl ether; toluene; acetonitrile;

DOI:10.1021/ja00228a067

upstream raw materials:

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

(4S,6R)-4-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-6-[2-((1S,2S,8aR)-2-methyl-8-triethylsilanyloxy-1,2,6,7,8,8a-hexahydro-naphthalen-1-yl)-ethyl]-[1,3]dioxane

4-[(1S,5S,6S)-6-(2-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-ethyl)-5-methyl-2-oxo-cyclohex-3-enyl]-4-triethylsilanyloxy-butyraldehyde

<4R-<4α*(1R^*,2S^*)>6α>>-6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-α-(2-methyl-5-oxo-3-cyclohexen-1-yl)-1,3-dioxane-4-propanal

Downstream raw materials:

mevastatin

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

<1S-<1α,7β,8β(4S*,6R*),8aβ>>-8-<2-<6-<2-<<(1,1-Dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>ethyl>-1,2,6,7,8,8a-hexahydro-7-methyl-1-naphthalenol