2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-3-(phenylsulfonyl)-, (1S,4R,5S,6S)-

Base Information

• Chemical Name: 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-3-(phenylsulfonyl)-, (1S,4R,5S,6S)-
• CAS No.: 476331-61-0
• Molecular Formula: C20H32O4SSi
• Molecular Weight: 396.623
• Mol file: 476331-61-0.mol

Synonyms:

Chemical Property of 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-3-(phenylsulfonyl)-, (1S,4R,5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-3-(phenylsulfonyl)-, (1S,4R,5S,6S)-

There total 19 articles about 2-Cyclohexen-1-ol, 5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-4,6-dimethyl-3-(phenylsulfonyl)-, (1S,4R,5S,6S)- 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: 84.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,2S,3S,6R)-5-benzenesulfonyl-2,6-dimethyl-cyclohex-4-ene-1,3-diol (476331-51-8) → (1S,4R,5S,6S)-3-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-cyclohex-2-enol (476331-61-0)

Guidance literature:

tert-butyldimethylsilyl chloride; (1S,2S,3S,6R)-5-benzenesulfonyl-2,6-dimethyl-cyclohex-4-ene-1,3-diol; With 1H-imidazole; In DMF (N,N-dimethyl-formamide); at 70 ℃; for 20h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

Reference yield:

[(3S,4S,5S,6R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-cyclohex-1-enesulfonyl]-benzene → (1S,4R,5S,6S)-3-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-cyclohex-2-enol (476331-61-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1021/ol026377m

Reference yield:

C12H11O3S(1-)*Li(1+) → (1S,4R,5S,6S)-3-benzenesulfonyl-5-(tert-butyl-dimethyl-silanyloxy)-4,6-dimethyl-cyclohex-2-enol (476331-61-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: tetrahydrofuran; diethyl ether / 0.5 h / -78 °C

1.2: 82 percent / tetrahydrofuran; diethyl ether / 8 h / 25 °C

2.1: Et₃N; TMSOTf / CH₂Cl₂ / 4 h / Heating

2.2: 89 percent / aq. m-CPBA / CH₂Cl₂ / 6 h

3.1: 94 percent / tert-butyl hydroperoxide / Mo(CO)6 / benzene; decane / 1.5 h / Heating

4.1: methyllithium; CuI / tetrahydrofuran; diethyl ether; toluene / -30 - 0 °C

4.2: 92 percent / tetrahydrofuran; diethyl ether; toluene / -78 - 10 °C

5.1: 95 percent / PPh₃; diethyl azodicarboxylate; HCO₂H / tetrahydrofuran / 2 h / 20 °C

6.1: imidazole / dimethylformamide / 20 h / 70 °C

7.1: 690 mg / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; formic acid; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; diethylazodicarboxylate; copper(l) iodide; hexacarbonyl molybdenum; methyllithium; In tetrahydrofuran; diethyl ether; decane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 5.1: Mitsunobu reaction;

DOI:10.1021/ol026377m

upstream raw materials:

(1S,5S,6S)-2-benzenesulfonyl-5-methyl-7-oxa-bicyclo[4.1.0]hept-2-ene

(1R,5S,6R)-5-benzenesulfonyl-6-methyl-3-phenylsulfanyl-cyclohex-3-enol

(6R)-2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-one

(5R)-5-methyl-2-(phenylthio)cyclohexan-1-one