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

Base Information

• Chemical Name: (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran
• CAS No.: 85443-49-8
• Molecular Formula: C50H44 O6
• Molecular Weight: 740.896
• European Community (EC) Number: 287-241-7
• DSSTox Substance ID: DTXSID20234668
• Nikkaji Number: J333.180F
• Wikidata: Q83116491
• Mol file: 85443-49-8.mol

Synonyms:85443-49-8;(2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran;EINECS 287-241-7;(2R,3S)-2-[3,4-bis(phenylmethoxy)phenyl]-3,5,7-tris(phenylmethoxy)-3,4-dihydro-2H-chromene;(2R-TRANS)-2-[3,4-BIS(PHENYLMETHOXY)PHENYL]-3,4-DIHYDRO-3,5,7-TRIS(PHENYLMETHOXY)-2H-1-BENZOPYRAN;2H-1-Benzopyran,2-[3,4-bis(phenylmethoxy)phenyl]-3,4-dihydro-3,5,7-tris(phenylmethoxy)-,(2R,3S)-;SCHEMBL18427309;DTXSID20234668;AKOS030243047;NS00038945

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

Chemical Property:

• Vapor Pressure: 1.6E-28mmHg at 25°C
• Boiling Point: 856.2°C at 760 mmHg
• Flash Point: 306.8°C
• PSA: 55.38000
• Density: 1.25g/cm³
• LogP: 11.26420
• Solubility.: Chloroform, DCM, Ethyl Acetate
• XLogP3: 10.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 16
• Exact Mass: 740.31378912
• Heavy Atom Count: 56
• Complexity: 1070

Purity/Quality:

99% ^*data from raw suppliers

(+)-3'',4'',3,5,7-Penta-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)OCC8=CC=CC=C8
• 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)OCC8=CC=CC=C8
• Uses: (+)-3'',4'',3,5,7-Penta-O-benzylcatechin is an intermediate in the synthesis of (+)-trans Taxifolin (T010005), an antioxidant flavenoid.

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

There total 8 articles about (2R-trans)-2-(3,4-Bis(phenylmethoxy)phenyl)-3,4-dihydro-3,5,7-tris(phenylmethoxy)-2H-1-benzopyran 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: 95.0%

benzyl bromide (100-39-0) + 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman (85443-49-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/j.bmcl.2004.11.046

Reference yield: 91.0%

benzyl chloride (100-44-7) + catechin (154-23-4) → (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman (85443-49-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; mineral oil; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2011.10.039

Reference yield: 81.0%

benzyl bromide (100-39-0) + benzyl chloride (100-44-7) + catechin (154-23-4) → (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman (85443-49-8)

Guidance literature:

benzyl chloride; catechin; With potassium carbonate; In N,N-dimethyl-formamide; at 130 ℃; for 3h;

benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

upstream raw materials:

benzyl bromide

benzyl chloride

catechin

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

Downstream raw materials:

C₅₅H₅₀O₈

C₂₀H₂₂O₈

C₁₈H₁₈O₈

C₁₈H₁₆O₇

Refernces

• 1、 Batchu, Venkateswara Rao,Dorigundla, Aravind Reddy,Gurrapu, Raju,Macha, Lingamurthy,Vanka, Umamaheswara Sarma. "Total Synthesis of the Natural Products Ulmoside A and (2 R,3 R)-Taxifolin-6- C -β- d -glucopyranoside". supporting information. p. 1097 - 1101. Retrieved 2020/07/03.
• 2、 Pariollaud, Marie,Cockrell, Jennifer,Selenski, Carolyn. "Total synthesis of (-)-bis-8,8′-catechinylmethane isolated from cocoa liquor". . p. 2484 - 2486. Retrieved 2014/05/06.