69082-83-3

Basic information

• Product Name: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan
• CAS NO: 69082-83-3
• Molecular Weight: 744.793
• Mol File: 69082-83-3.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(69082-83-3)
• EPA Substance Registry System: (2S,3R,4S)-2,3-trans-3,4-cis-3-acetoxy-4-<(2R,3S)-2,3-trans-3-acetoxy-3',4',5,7-tetramethoxyflavan-8-yl>-3',4',7-trimethoxyflavan(69082-83-3)

Safety Data

• Hazardous Substances Data: 69082-83-3(Hazardous Substances Data)

Upstream product

• 108-24-7 acetic anhydride 
• 78185-25-8 (2S,3R,4S,2'R,3'S)-2,2'-Bis-(3,4-dimethoxy-phenyl)-7,5',7'-trimethoxy-3,4,3',4'-tetrahydro-2H,2'H-[4,8']bichromenyl-3,3'-diol 
• 57499-11-3 (-)-fisetinidol-(4α,8)-(+)-catechin hepta-O-methyl 
• 186581-53-3 diazomethane 
• 57526-59-7 (2R,3S,4S)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',5,7-pentahydroxyflavan-8-yl>flavan 

Downstream Products

• 131266-32-5 4β-Hydroxy-tri-O-methyl-3-O-acetyl-(-)-fisetinidol-(4α,8)-tetra-O-methyl-3-O-acetyl-(+)-catechin 

Relevant articles and documents

Oligomeric flavanoids. Part 26. Structure and synthesis of the first profisetinidins with epifisetinidol constituent units

The natural occurrence of the first oligomeric profisetinidins with (2R,3R)-2,3-cis-epifisetinidol chain extender units is demonstrated in the bark of Pithecellobium dulce (Guamuchil). Semi-synthesis using the appropriate flavan-3-ol and flavan-3,4-diol precursors permits unequivocal structural and stereochemical assignment of the novel dimeric epifisetinidol-(4β,8)-catechin and epicatechins 16 and 18, the trimeric bis-epifisetinidol-(4β,6:4β,8)-catechin and epicatechins 33 and 35, the fisetinidol-(4α,8)-catechin-(6,4β)-epifisetinidol 37 and fisetinidol-(4α,8)-epicatechin-(6,4β)-epifisetinidol 39.

Synthesis of Condensed Tannins. Part 14. Biflavanoid Profisetinidins as Synthons. The Acid-Induced 'Phlobaphene'Reaction

Free phenolic - and -2,3-trans-(-)-fisetinidol-(+)-catechin diastereoisomers of both 3,4-trans and 3,4-cis configuration, which serve as synthons for higher oligomers, are available in improved yields from direct condensation, and also via novel 6-iodo-(+)-catechin as an intermediate substrate.Acid-induced transformations of the predominant -all-trans isomer, illustrative of the well-known 'phlobaphene reaction' of condensed tannins, is shown to include ring-isomerization and fission of the inter-flavanoid bond, followed in the latter instance by the alternatives of anthocyanidin formation, positional rearrangement and self-condensation.

Synthesis of Condensed Tannins. Part 5. The First Angular -Triflavanoids and Their Natural Counterparts

Angular triflavanoids comprising a group of four diastereoisomeric -bi--(+)-catechins with definable absolute configurations (2R,3S,4S-and 2R,3S,4R-2R,3S-2R,3S,4S; 2R,3S,4S- and 2R,3S,4R-2R,3S-2R,3S,4R) result from flavanyl-4-carbocation mediated condensation of (2R,3S,4R)-flavan-3,3',4,4',7-pentaol at C-6 of the (+)-catechin units of all-trans-(2R,3S,4S-2R,3S)--(-)-fisetinidol-(+)-catechin and its 3,4-cis-(2R,3S,4R-2R,3S) diastereomer respectively.The natural coexistence of some of the forementioned species of bi- and tri-flavanoids and their precursors indicate a comparable sequence of 4,8 preceding 4,6 condensation with (+)-catechin as common nucleophile.