37064-32-7

Basic information

• Product Name: 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)
• Synonyms: 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)
• CAS NO: 37064-32-7
• Molecular Weight: 690.744
• Mol File: 37064-32-7.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)(CAS DataBase Reference)
• NIST Chemistry Reference: 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)(37064-32-7)
• EPA Substance Registry System: 5,7,3',4'-tetra-O-methylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin)(37064-32-7)

Safety Data

• Hazardous Substances Data: 37064-32-7(Hazardous Substances Data)

Upstream product

• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 77-78-1 dimethyl sulfate 
• 299412-75-2 5,7,3',4'-tetra-O-benzylepicatechin-4β,8-(5,7,3',4'-tetra-O-methylepicatechin) 
• 29106-49-8 procyanidin B₂ 
• 186581-53-3 diazomethane 
• 22970-70-3 (2R,3R,4S)-2,3-cis-3,4-trans-3',4',5,7-tetramethoxyflavan-3,4-diol 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 

Downstream Products

• 3888-39-9 (2R,3R)-2,3-cis-3-acetoxy-8-<(2R,3R,4R)-2,3-cis-3,4-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-4-yl>-3',4',5,7-tetramethoxyflavan 

Relevant articles and documents

Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavan linkage regio- and stereochemistry by oxidative degradation of an O-alkylated derivative of procyanidin B2 to (R)-(-)-2,4-diphenylbutyric acid

The assignment of interflavan bond regio- and stereochemistry in oligomeric proanthocyanidins has in the past relied on empirical spectroscopic techniques which are influenced by the conformation of the C rings. Only recently was the 4,8-regiochemistry of procyanidin B2 (3b) firmly established by 2-dimensional NMR methods. We describe herein the proof of 4β-stereochemistry in 3b by oxidative degradation of the derivative 3d bearing differential (O-benzyl and O-methyl) protecting groups in its 'top' and 'bottom' epicatechin moieties, to (R)-(-)-2,4-diphenylbutyric acid. The key elements of the degradative process are (1) removal of the C-3 alcohol functions through a modified Barton deoxygenation employing hypophosphorous acid as the reducing agent; (2) deprotection of the 'top' unit by hydrogenolysis, followed by exhaustive aryl triflate formation with N,N-bis-(trifluoromethanesulfonyl)aniline and DBU in DMF; (3) hydrogenolytic deoxygenation of the 'top' unit over Pearlman's catalyst with concomitant scission of the O-C2 bond; (4) selective oxidation of the 'bottom' unit with NaIO4/RuCl3. The hitherto unreported absolute configuration of (-)-2,4-diphenylbutyric acid was established as R by X-ray crystal structure analysis of the (R)-(+)-α-methylbenzylamine salt. As a corollary, the selectivity of hydrogenolytic and solvolytic reactions of epicatechin-derived tetrasulfonates has been investigated.

Synthesis of Condensed Tannins. Part 12. Direct Access to - and -all-2,3-cis-Procyanidin Derivatives from (-)-Epicatechin: Assessment of Bonding Positions in Oligomeric Analogues from Crataegus oxyacantha L.

Synthesis of methyl ester acetates of - and -all-2,3-cis-procyanidin biflavanoids is effected by oxidative functionalization of (-)-epicatechin tetramethyl ester with lead tetra-acetate, and condensation of the resultant 2,3-cis-flavan-3,4-diol