(1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane

Base Information

• Chemical Name: (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane
• CAS No.: 140363-93-5
• Molecular Formula: C₁₆H₂₂O₆S
• Molecular Weight: 342.413
• Mol file: 140363-93-5.mol

Synonyms:(1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane

Chemical Property of (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane

There total 1 articles about (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane 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: 93.0%

(1S,3S,5R)-1-acetoxy-5-benzyloxy-3-cyclohexanol (130256-36-9,137331-22-7) + methanesulfonyl chloride (124-63-0) → (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane (140363-93-5)

Guidance literature:

With pyridine; at 0 ℃; for 16h;

DOI:10.1016/S0957-4166(00)80209-8

Reference yield: 84.0%

cesium acetate (3396-11-0) + (1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane (140363-93-5) → (1R,3R,5R)-1,3-diacetoxy-5-benzyloxycyclohexane (130256-34-7,131321-51-2)

Guidance literature:

With 18-crown-6 ether; In benzene; for 2.5h; Heating;

DOI:10.1016/S0957-4166(00)80209-8

Reference yield:

(1R,3S,5S)-1-acetoxy-5-benzyloxy-3-methanesulfonyloxycyclohexane (140363-93-5) → (3S,5R)-5-acetoxy-3-benzoyloxy-1-cyclohexene (131245-89-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / 18-crown-6 / benzene / 2.5 h / Heating

2: 99 percent / H₂ / 10percent Pd/C / methanol

3: 1.) trifluoromethanesulfonic anhydride, pyridine, 2.) SiO₂ / 1.) 0 deg C, 2 h

4: 77 percent / 0.1 M phosphate buffer / 5.5 h / 30 °C / pH 7.0, Pseudomonas fluorescens lipase

5: 97 percent / pyridine

With pyridine; phosphate buffer; 18-crown-6 ether; hydrogen; silica gel; trifluoromethanesulfonic acid anhydride; palladium on activated charcoal; In methanol; benzene;

DOI:10.1016/S0957-4166(00)80209-8

upstream raw materials:

(1S,3S,5R)-1-acetoxy-5-benzyloxy-3-cyclohexanol

methanesulfonyl chloride

Downstream raw materials:

(1R,3R,5R)-1,3-diacetoxy-5-benzyloxycyclohexane

(3S,5R)-5-acetoxy-1-cyclohexen-3-ol

(3S,5R)-3,5-diacetoxy-1-cyclohexene

(1R,3R)-1,3-diacetoxy-5-hydroxy-cyclohexane