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

Base Information

• Chemical Name: Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-yl ester
• CAS No.: 123568-12-7
• Molecular Formula: C₂₂H₃₆O₆S₂Si
• Molecular Weight: 488.742
• Mol file: 123568-12-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-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: 100.0%

(3aR,4S)-7a-Benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-ol (123567-97-5) + methanesulfonyl chloride (124-63-0) → Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-yl ester (123568-12-7)

Guidance literature:

With triethylamine; In dichloromethane; at 25 ℃; for 2h;

DOI:10.1021/jo00288a058

Reference yield:

3-(tert-butyldimethylsilyloxy)-1-(phenylsulfonyl)cyclohexene (70810-37-6) → Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-yl ester (123568-12-7)

Guidance literature:

Multi-step reaction with 5 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

5: 100 percent / NEt₃ / CH₂Cl₂ / 2 h / 25 °C

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

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) → Methanesulfonic acid (3aR,4S)-7a-benzenesulfonyl-4-(tert-butyl-dimethyl-silanyloxy)-octahydro-inden-1-yl ester (123568-12-7)

Guidance literature:

Multi-step reaction with 4 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

4: 100 percent / NEt₃ / CH₂Cl₂ / 2 h / 25 °C

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

DOI:10.1021/jo00288a058

upstream raw materials:

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

methanesulfonyl chloride

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

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