(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

Base Information

• Chemical Name: (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
• CAS No.: 116996-36-2
• Molecular Formula: C₄₃H₆₆O₄Si₂
• Molecular Weight: 703.166
• Mol file: 116996-36-2.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 6 articles about (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 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: 85.0%

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) → (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 (116996-36-2,117065-47-1)

Guidance literature:

With titanium(III) chloride; In 1,2-dimethoxyethane; 1.) RT, 5 h, 2.) reflux, 3 h;

DOI:10.1021/ja00164a024

Reference yield:

triethylsilyl chloride (994-30-9) → (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 (116996-36-2,117065-47-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / i-Pr₂NH / DMAP / diethyl ether / 36 h / Ambient temperature

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

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

With titanium(III) chloride; ozone; diisopropylamine; triphenylphosphine; dmap; In 1,2-dimethoxyethane; diethyl ether;

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) → (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 (116996-36-2,117065-47-1)

Guidance literature:

Multi-step reaction with 5 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

With Wilkinson's catalyst; titanium(III) chloride; ozone; diisopropylamine; triphenylphosphine; lithium diisopropyl amide; dmap; In 1,2-dimethoxyethane; diethyl ether; toluene; acetonitrile;

DOI:10.1021/ja00228a067

upstream raw materials:

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

triethylsilyl chloride

<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

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

Downstream raw materials:

<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

(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

(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

mevastatin