882867-43-8

Basic information

• Product Name: (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol
• Synonyms: (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol
• CAS NO: 882867-43-8
• Molecular Weight: 738.877
• Mol File: 882867-43-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol(882867-43-8)
• EPA Substance Registry System: (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-ol(882867-43-8)

Safety Data

• Hazardous Substances Data: 882867-43-8(Hazardous Substances Data)

Upstream product

• 154-23-4 catechin 
• 100-44-7 benzyl chloride 
• 110-80-5 2-ethoxy-ethanol 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 

Downstream Products

• 882867-44-9 Acetic acid (2R,3S)-5,7-bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-4-(2-ethoxy-ethoxy)-chroman-3-yl ester 

Relevant articles and documents

Influence of an 8-trifluoroacetyl group on flavanol couplings

The effect of an electron attracting substituent in the Lewis acid catalyzed oligomerization of flavanols was investigated. The results showed that the presence of a COCF3, at the 8 position of a (+)-catechin unit strongly influenced the attack of the 6 free nucleophile flavanol position by the electrophile generated from a 4-O-alkyloxy protected catechin unit. This was observed either with TiCl4 or TMSOTf as Lewis acids in which the carbon-carbon bond formation was inhibited and the corresponding dimer was detected in small amount. On the contrary, the formation of a carbon-oxygen bond was observed and the corresponding C-4→O→C-3 ether linked procyanidin dimer was isolated in a good yield. In order to avoid the participation of the C-3 hydroxyl group in the dimerization reaction, the two flavanol units were forced into C-4→C-8 coupling by use of an internal link. The structural elucidation of the isolated compounds was achieved through MS and NMR spectroscopy.