(2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Base Information

• Chemical Name: (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene
• CAS No.: 96247-02-8
• Molecular Formula: C₁₆H₁₆O₅
• Molecular Weight: 288.3
• Mol file: 96247-02-8.mol

Synonyms:(2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Chemical Property of (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

There total 13 articles about (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene 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: 80.0%

Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester (175979-30-3) → (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (96247-02-8)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1016/0957-4166(96)00004-3

Reference yield: 29.0%

(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (86782-19-6) → (2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (71481-04-4) + (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (96247-02-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol;

DOI:10.1246/bcsj.59.655

Reference yield: 19.0%

(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (86782-19-6) → (2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (71481-04-4) + (2R)-trans-3-acetoxy-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (96247-03-9) + (2R)-trans-2-acetoxy-3-hydroxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (96247-02-8)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; at 15 - 20 ℃; for 72h;

DOI:10.1021/jo00213a030

upstream raw materials:

(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene

Benzoic acid (5R,6R)-6-acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-cyclohexa-1,3-dienylmethyl ester

(1R,2R,3S)-1,2-O-Cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

(1R,2R,3S)-3-O-tert-Butyldimethylsilyl-1,2-O-cyclohexylidene-5-hydroxymethyl-4-cyclohexen-1,2,3-triol

Downstream raw materials:

Benzoic acid (1S,4S,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

Benzoic acid (1R,4R,7S,8S)-7-acetoxy-8-hydroxy-2,3-dioxa-bicyclo[2.2.2]oct-5-en-1-ylmethyl ester

Benzoic acid (1S,2S,4S,5S,6R,7S)-5-acetoxy-6-hydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4]oct-4-ylmethyl ester

(1R-(1α,2α,4α,5β,6α,7α))-4-[(benzoyloxy)methyl]-3,8-dioxatricyclo[5,1,0,0^2,4]octane-5,6-diyl diacetate