(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Base Information

• Chemical Name: (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate
• CAS No.: 256236-30-3
• Molecular Formula: C₇₁H₆₀O₁₀
• Molecular Weight: 1073.25
• Mol file: 256236-30-3.mol

Synonyms:(-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Chemical Property of (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate

There total 11 articles about (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-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: 96.0%

3,4,5-tribenzyloxybenzoic acid (1486-48-2) + 5,7,3',4'-tetra-O-benzylepicatechin (87292-49-7) → (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.bmc.2005.02.023

Reference yield: 80.0%

3,4,5-tris(benzyloxy)benzoyl chloride (1486-47-1) + 5,7,3',4'-tetra-O-benzylepicatechin (87292-49-7) → (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃;

DOI:10.1016/j.bmc.2004.04.033

Reference yield:

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → (-)-(2R,3R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate (256236-30-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

2: 90 percent / L-Selectride / tetrahydrofuran / -78 °C

3: 80 percent / DMAP / CH₂Cl₂ / 20 °C

With dmap; L-Selectride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 1: Dess-Martin oxidation;

DOI:10.1016/j.bmc.2004.04.033

upstream raw materials:

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

5,7,3',4'-tetra-O-benzylepicatechin

3,4,5-tribenzyloxybenzoic acid

3,4-dibenzyloxybenzaldehyde

Downstream raw materials:

[4,8]-2,3-trans-3,4-trans:2,3-cis-octa-O-benzyl-(+)-catechin-(-)-epicatechin-3,3''-di-O-(tri-O-benzyl)gallate

5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin-(4β,8β)-[5,7,3',4'-tetra-O-benzyl-3-O-(3,4,5-tri-O-benzylgalloyl)-(-)-epicatechin]

(-)-epicatechin gallate