(2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one

Base Information

• Chemical Name: (2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one
• CAS No.: 87292-54-4
• Molecular Formula: C43H36O6
• Molecular Weight: 648.755
• DSSTox Substance ID: DTXSID90456810
• Nikkaji Number: J1.248.455K
• Wikidata: Q82279384
• Mol file: 87292-54-4.mol

Synonyms:87292-54-4;SCHEMBL4618868;DTXSID90456810;(2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one;(2R)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-4H-chromen-3-one

Chemical Property of (2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one

Chemical Property:

• XLogP3: 9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 648.25118886
• Heavy Atom Count: 49
• Complexity: 963

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)C(OC2=C1C(=CC(=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)C5=CC(=C(C=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7
• Isomeric SMILES: C1C(=O)[C@H](OC2=C1C(=CC(=C2)OCC3=CC=CC=C3)OCC4=CC=CC=C4)C5=CC(=C(C=C5)OCC6=CC=CC=C6)OCC7=CC=CC=C7

Technology Process of (2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one

There total 16 articles about (2R)-2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3-one 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: 92.0%

5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one (87292-54-4)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; for 1.83333h;

Reference yield:

benzyl bromide (100-39-0) → (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one (87292-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / -10 - 20 °C

2: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With potassium carbonate; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201000482

Reference yield:

catechin (154-23-4) → (+)-(2R)-5,7-bis(benzyloxy)-2-[3,4-bis(benzyloxy)phenyl]chroman-3-one (87292-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium carbonate / N,N-dimethyl-formamide / -10 - 20 °C

2: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With potassium carbonate; Dess-Martin periodane; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201000482

upstream raw materials:

5,7,3',4'-tetra-O-benzyl-(+)-catechin

3,4-dibenzyloxybenzaldehyde

1,3-dibenzylphloroglucinol

3-(3,4-bis-benzyloxy-phenyl)-acrylic acid ethyl ester

Downstream raw materials:

(2R,3R,4S)-5,7,3',4'-tetrabenzyloxy-4-(2''-ethoxyethoxy)flavan-3-ol

C₂₅H₂₄O₁₁

5,7,3',4'-tetra-O-benzyl-3-(3'',4'',5''-trimethoxybenzoyl)-(-)-epicatechin

C₅₆H₆₂O₈Si