(2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol

Base Information

• Chemical Name: (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol
• CAS No.: 20728-73-8
• Molecular Formula: C43H38 O6
• Molecular Weight: 650.771
• Hs Code.: 2932999099
• European Community (EC) Number: 243-993-8
• DSSTox Substance ID: DTXSID20942938
• Nikkaji Number: J225.317H
• Wikidata: Q82919934
• Mol file: 20728-73-8.mol

Synonyms:20728-73-8;EINECS 243-993-8;(2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol;5,7,3',4'-tetra-o-benzylcatechin;(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-5,7-bis(phenylmethoxy)-3,4-dihydro-2H-chromen-3-ol;Rel-(2R,3S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-ol;2H-1-Benzopyran-3-ol, 2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-5,7-bis(phenylmethoxy)-, (2R,3S)-;318949-07-4;(2R-TRANS)-2-[3,4-BIS(PHENYLMETHOXY)PHENYL]-3,4-DIHYDRO-5,7-BIS(PHENYLMETHOXY)-2H-1-BENZOPYRAN-3-OL;SCHEMBL4640426;DTXSID20942938;NRJRMFXLQSNZGY-PWPASLGISA-N;C43H38O6;AKOS030241750;C43-H38-O6;J-013555;2alpha-[3,4-Bis(benzyloxy)phenyl]-5,7-bis(benzyloxy)chroman-3beta-ol;5,7-BIS(BENZYLOXY)-2-[3,4-BIS(BENZYLOXY)PHENYL]-3,4-DIHYDRO-2H-1-BENZOPYRAN-3-OL

Chemical Property of (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 813.8°Cat760mmHg
• Flash Point: 445.9°C
• PSA: 66.38000
• Density: 1.234g/cm³
• LogP: 9.03970
• Solubility.: Dichloromethane, Ethyl Acetate, Methanol
• XLogP3: 7.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 650.26683893
• Heavy Atom Count: 49
• Complexity: 921

Purity/Quality:

99% ^*data from raw suppliers

5,7,3'',4''-Tetra-O-benzylcatechin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(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)O
• Isomeric SMILES: C1[C@@H]([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)O
• Uses: Protected (+)-Catechin (C217500).

Technology Process of (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol

There total 32 articles about (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-5,7-bis(phenylmethoxy)-2H-1-benzopyran-3-ol 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: 98.0%

benzyl chloride (100-44-7) + catechin (154-23-4) → 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at -78 - 20 ℃;

DOI:10.1080/00304940409355371

Reference yield: 94.0%

(2R,3R)-2,3-Bis-benzoyloxy-succinic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yl ester methyl ester (318949-09-6) → 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8)

Guidance literature:

With potassium hydroxide; water; In methanol;

DOI:10.1016/S0040-4039(00)01649-X

Reference yield: 85.0%

(+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol (732298-11-2) → 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8)

Guidance literature:

(+)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4-bis(benzyloxy)phenyl]propane-1,2-diol; With pyridinium p-toluenesulfonate; orthoformic acid triethyl ester; In 1,2-dichloro-ethane; at 20 - 60 ℃; for 5.33333h;

With methanol; potassium carbonate; In 1,2-dimethoxyethane; at 20 ℃; for 18h;

DOI:10.1002/ejoc.200800886

upstream raw materials:

(2R,3S)-5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman-3-yl acetate

benzyl bromide

catechin

(2R,3R)-2,3-Bis-benzoyloxy-succinic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yl ester methyl ester

Downstream raw materials:

[(2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-chroman-3-yloxy]-tert-butyl-dimethyl-silane

catechin

C₈₅⁽¹³⁾CH₇₄O₁₂

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