((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane

Base Information

• Chemical Name: ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane
• CAS No.: 123538-59-0
• Molecular Formula: C₂₂H₃₄O₃SSi
• Molecular Weight: 406.662
• Mol file: 123538-59-0.mol

Synonyms:((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane

Chemical Property of ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane

There total 8 articles about ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane 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: 70.0%

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane (72047-94-0) + (R)-3-(tert-Butyldimethylsiloxy)-1-(phenylsulfonyl)cyclohexene (123488-44-8) → ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane (123538-59-0)

Guidance literature:

palladium diacetate; triisopropyl phosphite; In toluene; at 80 ℃; for 40h;

DOI:10.1021/ja00201a032

Reference yield:

3-(phenylsulfanyl)cyclohex-2-en-1-one (75717-39-4) → ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane (123538-59-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / (-)-N-Methylephedrine, LAH, 2-(Ethylamino)pyridine / diethyl ether / 3 h / -78 °C

2: 74 percent / MCPBA / CH₂Cl₂ / 1.) 1 h, 0 degC, 2.) 0.5 h, room temp.

3: imidazole / dimethylformamide / 5 h / Ambient temperature

4: 70 percent / (i-C₃H₇O)3P, Pd(OAc)2 / toluene / 40 h / 80 °C

With 1H-imidazole; 2-(ethylamino)pyridine; lithium aluminium tetrahydride; (-)-N-methylephedrine; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; triisopropyl phosphite; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja00201a032

Reference yield:

1,3-cylohexanedione (504-02-9) → ((3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-yloxy)-tert-butyl-dimethyl-silane (123538-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 75 percent / TsOH / benzene

2: 62 percent / (-)-N-Methylephedrine, LAH, 2-(Ethylamino)pyridine / diethyl ether / 3 h / -78 °C

3: 74 percent / MCPBA / CH₂Cl₂ / 1.) 1 h, 0 degC, 2.) 0.5 h, room temp.

4: imidazole / dimethylformamide / 5 h / Ambient temperature

5: 70 percent / (i-C₃H₇O)3P, Pd(OAc)2 / toluene / 40 h / 80 °C

With 1H-imidazole; 2-(ethylamino)pyridine; lithium aluminium tetrahydride; (-)-N-methylephedrine; toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; palladium diacetate; triisopropyl phosphite; In diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ja00201a032

upstream raw materials:

[2-(acetoxymethyl)prop-2-enyl]trimethylsilane

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

(R)-3-(tert-Butyldimethylsiloxy)-1-(phenylsulfonyl)cyclohexene

3-(phenylsulfanyl)cyclohex-2-en-1-one

Downstream raw materials:

(3aS,4R,7aR)-7a-Benzenesulfonyl-2-methylene-octahydro-inden-4-ol

2-Methylene-7aβ-(phenylsulfonyl)-3aβ-octahydroinden-4-one

(S)-Methoxy-phenyl-acetic acid (3aR,4S)-2-oxo-3,3a,4,5,6,7-hexahydro-2H-inden-4-yl ester

(S)-Methoxy-phenyl-acetic acid (3aR,4R)-2-oxo-3,3a,4,5,6,7-hexahydro-2H-inden-4-yl ester