(-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate

Base Information

• Chemical Name: (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate
• CAS No.: 1350896-02-4
• Molecular Formula: C₄₃H₃₆O₆
• Molecular Weight: 648.755
• Mol file: 1350896-02-4.mol

Synonyms:(-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate

Chemical Property of (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate

There total 3 articles about (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate 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:

3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) + (-)-epicatechin → C43H36O6 (1350896-01-3) + (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate (1350896-02-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1016/j.bmcl.2011.09.116

Reference yield:

(1R,2R)-3-(2-hydroxyphenyl)-1-phenylpropane-1,2-diol (1350895-99-6) → (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate (1350896-02-4)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 14 h

2: triethylamine; dmap / dichloromethane / 15 h

With dmap; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 1: |Mitsunobu Displacement;

DOI:10.1016/j.tet.2014.03.052

Reference yield:

(2S,3R)-trans-flavan-3-ol (184713-81-3) + 3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) → (-)-trans-(2S,3R)-phenylflavan-3-yl-3,4,5-tris(benzyloxy)benzoate (1350896-02-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 15h;

DOI:10.1016/j.tet.2014.03.052

upstream raw materials:

3,4,5-tris(benzyloxy)benzoyl chloride

(2S,3R)-trans-flavan-3-ol

(1R,2R)-3-(2-hydroxyphenyl)-1-phenylpropane-1,2-diol

Downstream raw materials:

(-)-(2S,3R)-trans-phenylflavan-3-yl-O-gallate