(2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

Base Information

• Chemical Name: (2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene
• CAS No.: 99232-68-5
• Molecular Formula: C₂₃H₂₀O₅
• Molecular Weight: 376.409
• Mol file: 99232-68-5.mol

Synonyms:(2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

Chemical Property of (2R)-trans-3-<(E)-cinnamoyloxy>-2-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-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

There total 3 articles about (2R)-trans-3-<(E)-cinnamoyloxy>-2-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: 27.0%

(2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (71481-04-4) + Cinnamoyl chloride (102-92-1,17082-09-6) → (2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (99232-68-5)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1246/bcsj.59.655

Reference yield: 24.0%

(2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (71481-04-4) + Cinnamoyl chloride (102-92-1,17082-09-6) → (2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (99232-68-5) + (2R)-trans-2-<(E)-cinnamoyloxy>-3-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene + (2R)-trans-2,3-bis<(E)-cinnamoyloxy>-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

Guidance literature:

With pyridine; In dichloromethane; a) 0 deg C, 1 h, b) RT, 2 h;

DOI:10.1021/jo00225a015

Reference yield:

(2R)-trans-2,3-diacetoxy-1-[(benzoyloxy)methyl]cyclohexa-4,6-diene (86782-19-6) → (2R)-trans-3-<(E)-cinnamoyloxy>-2-hydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene (99232-68-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / p-toluenesulfonic acid / methanol

2: 27 percent / CH₂Cl₂; pyridine / 0.5 h / 0 °C

With toluene-4-sulfonic acid; In pyridine; methanol; dichloromethane;

DOI:10.1246/bcsj.59.655

upstream raw materials:

(2R)-trans-2,3-dihydroxy-1-<(benzoyloxy)methyl>cyclohexa-4,6-diene

Cinnamoyl chloride

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

Downstream raw materials:

Zeylena