78376-75-7

Basic information

• Product Name: 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin
• Synonyms: 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin
• CAS NO: 78376-75-7
• Molecular Weight: 436.505
• Mol File: 78376-75-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin(CAS DataBase Reference)
• NIST Chemistry Reference: 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin(78376-75-7)
• EPA Substance Registry System: 3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin(78376-75-7)

Safety Data

• Hazardous Substances Data: 78376-75-7(Hazardous Substances Data)

Upstream product

• 154-23-4 catechin 
• 620-05-3 iodomethylbenzene 
• 78376-73-5 6,8-dibromo-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 51079-25-5 (2R,3S)-(+)-catechin 3',4',5,7-tetramethyl ether 
• 23671-72-9 8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 100-52-7 benzaldehyde 
• 28699-20-9 3-O-benzyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-42-2 3-O-benzyl-6,8-dibromo-3',4',5,7-tetra-O-methyl-(+)-catechin 

Downstream Products

• 69119-52-4 8-hydroxy-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-57-9 8-methoxycarbonyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-54-6 8-acetoxy-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-58-0 3-O-acetyl-8-methoxycarbonyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-55-7 8-acetoxy-3-O-acetyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-51-3 3-O-benzyl-8-hydroxy-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-56-8 3-O-benzyl-8-methoxycarbonyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-53-5 8-acetoxy-3-O-benzyl-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 28699-20-9 3-O-benzyl-8-bromo-3',4',5,7-tetra-O-methyl-(+)-catechin 
• 69119-42-2 3-O-benzyl-6,8-dibromo-3',4',5,7-tetra-O-methyl-(+)-catechin 

Relevant articles and documents

Studies in polyphenol chemistry and bioactivity. 3. Stereocontrolled synthesis of epicatechin-4α,8-epicatechin, an unnatural isomer of the B-type procyanidins

Oligomeric procyanidins containing 4α-linked epicatechin units are rare in nature and have hitherto not been accessible through stereoselective synthesis. We report herein the preparation of the prototypical dimer, epicatechin-4α,8-epicatechin (6), by reaction of the protected 4-ketones 11a,b with aryllithium reagents derived by halogen/metal exchange from the awl bromides 26a,b. Removal of the 4-hydroxyl group from the resulting tertiary benzylic alcohols 27a,b was effected by tri-n-butyltin hydride and trifluoroacetic acid in a completely stereoselective manner, resulting in hydride delivery exclusively from the β face. If benzyl was chosen for protection of the 3-hydroxyls, all protective groups could subsequently be removed in a single step by hydrogenolysis, tert-Butyldimethylsilyl groups, on the other hand, permitted selective deprotection of the 3-hydroxyls in preparation for their subsequent acylation with tri-O-benzylgalloyl chloride. Only monogalloylation at the "bottom" 3-hydroxyl took place when 28c was acylated under the previously reported conditions, reflecting the increased steric hindrance of the "top" 3-hydroxyl group in 28c compared with its 4β,8-isomer 3. The preparation of compounds 14 and 17 containing phloroglucinol trimethyl ether in the 4α and 4β linkages to epicatechin is also described. The 8-position of the bromine atom in 19, previously conjectured in analogy to the structurally characterized tetramethyl ether 20, was confirmed by transformation of both compounds into the common derivative 25.