(-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane

Base Information

• Chemical Name: (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane
• CAS No.: 186703-34-4
• Molecular Formula: C₃₅H₄₄O₆SSi
• Molecular Weight: 620.882
• Mol file: 186703-34-4.mol

Synonyms:(-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane

Chemical Property of (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane

There total 2 articles about (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane 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: 90.0%

p-toluenesulfonyl chloride (98-59-9) + (-)-(1S,2R,4S,6R)-1,2-cyclohexyldienedioxy-4-(tert-butyldiphenylsilyloxy)cyclohexan-6-ol (186703-33-3) → (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane (186703-34-4)

Guidance literature:

With dmap; TEA; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran;

DOI:10.1016/S0040-4039(96)02229-0

Reference yield:

(1S,2R,6R)-1,2-Cyclohexylidenedioxycyclohexane-4,6-diol → (-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane (186703-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 48 percent / Et₃N; DMAP / CH₂Cl₂ / 16 h / 20 °C

2: 67 percent / Et₃N; DMAP / CH₂Cl₂ / 72 h / 20 °C

With dmap; triethylamine; In dichloromethane; 1: Etherification / 2: Tosylation;

DOI:10.1039/a909292g

Reference yield: 100.0%

(-)-(1R,2R,4S,6R)-1,2-Cyclohexylidenedioxy-4-(tert-butyldiphenylsilyl)-6-(4'-methylphenylsulfonyloxy)cyclohexane (186703-34-4) → (-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-6-(4'-methylphenylsulfonyloxy)cyclohexan-4-ol (186703-35-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(96)02229-0

upstream raw materials:

p-toluenesulfonyl chloride

(-)-(1S,2R,4S,6R)-1,2-cyclohexyldienedioxy-4-(tert-butyldiphenylsilyloxy)cyclohexan-6-ol

Downstream raw materials:

(-)-(1R,2R,4R,6R)-1,2-Cyclohexylidenedioxy-6-(4'-methylphenylsulfonyloxy)cyclohexan-4-ol

(+)-(1S,2R,4R,6R)-4-Benzyloxy-1,6-epoxycyclohexan-2-ol

(+)-(1S,2R,4R,6R)-2,4-Bis(benzyloxy)-1,6-epoxycyclohexane

(-)-(1S,2R,4S,6R)-2,4-Bis(benzyloxy)-6-propyloxycyclohexanol