332386-71-7

Basic information

• Product Name: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol
• Synonyms: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol
• CAS NO: 332386-71-7
• Molecular Weight: 756.895
• Mol File: 332386-71-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol(332386-71-7)
• EPA Substance Registry System: (-)-(2R,3S)-trans-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol(332386-71-7)

Safety Data

• Hazardous Substances Data: 332386-71-7(Hazardous Substances Data)

Upstream product

• 332386-60-4 (-)-(1S,2S)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol 
• 942122-64-7 (1S,2S)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propane-1,2-diol 
• 332386-55-7 (E)-3-[2,4-bis(benzyloxy)-6-(tert-butyldimethylsilyloxy)phenyl]-1-[3,4,5-tris(benzyloxy)phenyl]propene 
• 332386-61-5 (E)-3-[2,4-bis(benzyloxy)-6-hydroxyphenyl]-1-[3,4,5-tris(benzyloxy)phenyl]-propene 
• 332386-68-2 (E)-3-[3,4,5-tris(benzyloxy)phenyl]prop-2-en-1-ol 
• 70424-94-1 methyl 3,4,5-tris(benzyloxy)benzoate 
• 79831-88-2 3,4,5-tribenzyloxybenzyl alcohol 
• 332386-67-1 ethyl (E)-3,4,5-tris(benzyloxy)cinnamate 

Downstream Products

• 2596-50-1 (-)-epigallocathechin gallate 
• 332386-74-0 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-ol 
• 332386-77-3 (-)-(2R,3R)-cis-5,7-bis(benzyloxy)-2-[3,4,5-tris(benzyloxy)phenyl]chroman-3-yl 3,4,5-tris(benzyloxy)benzoate 
• 1229517-68-3 2,3-trans-3,4-cis-4,5,7,3',4',5'-hexakis(benzyloxy)flavan-3-ol 
• 1499158-41-6 [4,8’]-2,3-cis-3.4-trans:2',3'-trans-3-acetoxydecabenzyloxy-(-)-epigallocatechin-(+)-gallocatechin 
• 1429125-62-1 (2R,3S,4S)-3-acetoxy-4-methoxy-5,7-3',4',5'-pentabenzyloxyflavan 

Relevant articles and documents

Stereoselective synthesis of benzylated prodelphinidins and their diastereomers with use of the mitsunobu reaction in the preparation of their gallocatechin precursors

The tetrabenzylated catechin 9 was prepared by benzylation of the commercially available pure (+)-catechin (3) and cou-pled with the commercially unavailable pentabenzylated (-)-gallocatechin 10, prepared in a one-step Mitsunobu-type cyclization of the triol 8. The highly stereoselective synthesis of benzylated prodelphinidins - catechin-(4α→8)-gallocate-chin (13), gallocatechin-(4α→8)-gallocatechin (14), and gallo-catechin- (4α→8)-catechin (15) - is reported for the first time. The ESI(+)-CID mass spectra of the coupling products were found to feature regioselective retro-Diels-Alder (RDA) reac-tions and unusual sequential losses of pairs of C7H7' radicals (182 u) from the Na+ adduct ions.

Enantioselective synthesis of epigallocatechin-3-gallate (EGCG), the active polyphenol component from green tea.

[reaction: see text]. Enantioselective synthesis of epigallocatechin-3-gallate (EGCG, 3b), the active polyphenol component from green tea, has been achieved by using a stereospecific cyclization of the Sharpless asymmetric dihydroxylation product 7c as the key step.