(1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane

Base Information

• Chemical Name: (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane
• CAS No.: 327189-67-3
• Molecular Formula: C₁₄H₂₈O₄Si
• Molecular Weight: 288.459
• Mol file: 327189-67-3.mol

Synonyms:(1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane

Chemical Property of (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane

There total 7 articles about (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-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: 100.0%

vinyl acetate (108-05-4,9003-20-7) + all-cis-5-(tert-butyldimethyl-silanyloxy)-cyclohexane-1,3-diol (187266-42-8,327189-66-2) → (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane (327189-67-3)

Guidance literature:

With Lipase QL; In ethyl acetate; at 20 ℃; for 46h;

DOI:10.1016/S0957-4166(00)00368-2

Reference yield: 55.0%

all-cis-5-((Tert-butyldimethylsilyl)oxy)cyclohexane-1,3-diol → (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane (327189-67-3)

Guidance literature:

In ethyl acetate;

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (1R,3S,5S)-1-acetoxy-3-hydroxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane (327189-67-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N / 4-dimethylaminopyridine / CH₂Cl₂ / 36 h / 25 °C

2: porcine liver esterase / 2-methyl-propan-2-ol; aq. phosphate buffer / 48 h / 25 °C / pH 8

With porcine liver esterase; triethylamine; dmap; In phosphate buffer; dichloromethane; tert-butyl alcohol;

DOI:10.1021/ja0685708

upstream raw materials:

vinyl acetate

all-cis-5-(tert-butyldimethyl-silanyloxy)-cyclohexane-1,3-diol

cis,cis-3-(methyl-carbonyloxy)-5-(tert-butyl-dimethylsilyloxy)-cyclohexyl acetate

tert-butyldimethylsilyl chloride

Downstream raw materials:

5-tert-butyl-dimethylsilyloxy-(5S)-2-cyclohexenone