(3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol

Base Information

• Chemical Name: (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol
• CAS No.: 123567-97-5
• Molecular Formula: C₂₁H₃₄O₄SSi
• Molecular Weight: 410.65
• Mol file: 123567-97-5.mol

Synonyms:(3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol

Chemical Property of (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol

There total 5 articles about (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol 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: 78.0%

3-[(1R,6S)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-trimethylsilanyl-cyclohexyl]-propionaldehyde (123567-95-3,123670-11-1) → (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol (123567-97-5)

Guidance literature:

With tetrabutyl ammonium fluoride; 4 A molecular sieve; In diethyl ether; at 25 ℃; for 1.5h;

DOI:10.1021/jo00288a058

Reference yield:

3-(tert-butyldimethylsilyloxy)-1-(phenylsulfonyl)cyclohexene (70810-37-6) → (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol (123567-97-5)

Guidance literature:

Multi-step reaction with 4 steps

2: 1. BH₃SMe₂ 2. 10percent H₂O₂, 10percent NaOH / 1. THF, 0 deg C - 25 deg C, 0.5 h 2. CH₂Cl₂, 0 deg C - 25 deg C, 1 h

3: Swern oxidation

4: 78 percent / tetra-n-butylammonium fluoride / molecular sieves (4 Angstroem) / diethyl ether / 1.5 h / 25 °C

With sodium hydroxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; 4 A molecular sieve; In diethyl ether;

DOI:10.1021/jo00288a058

Reference yield:

[(2R,3S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-cyclohexanesulfonyl]-benzene (123568-11-6,123670-09-7) → (3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol (123567-97-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1. BH₃SMe₂ 2. 10percent H₂O₂, 10percent NaOH / 1. THF, 0 deg C - 25 deg C, 0.5 h 2. CH₂Cl₂, 0 deg C - 25 deg C, 1 h

2: Swern oxidation

3: 78 percent / tetra-n-butylammonium fluoride / molecular sieves (4 Angstroem) / diethyl ether / 1.5 h / 25 °C

With sodium hydroxide; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; 4 A molecular sieve; In diethyl ether;

DOI:10.1021/jo00288a058

upstream raw materials:

3-[(1R,6S)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-trimethylsilanyl-cyclohexyl]-propionaldehyde

3-(tert-butyldimethylsilyloxy)-1-(phenylsulfonyl)cyclohexene

[(2R,3S)-2-Allyl-3-(tert-butyl-dimethyl-silanyloxy)-1-trimethylsilanyl-cyclohexanesulfonyl]-benzene

3-[(1R,6S)-2-Benzenesulfonyl-6-(tert-butyl-dimethyl-silanyloxy)-2-trimethylsilanyl-cyclohexyl]-propan-1-ol

Downstream raw materials:

Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-yl ester