127644-35-3

Upstream product

• 490-49-3 fisetinidol 
• 967-27-1 (+)-mollisacacidin 
• 78139-48-7 (2R,3S,4R)-2,3-trans-3,4-trans-3,3',4',7-tetrahydroxy-4-<(2R,3S)-2,3-trans-3,3',4',7-tetrahydroxyflavan-6-yl>flavan 

Downstream Products

• 127644-51-3 (2S,3S,4R,7S,8R)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,7-diol 
• 127644-53-5 (2S,3S,4R,7S,8S)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,7-diol 
• 127644-49-9 (2R,3S,4R,7S,8S)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,7-diol 
• 78185-31-6 (2R,3S,4S)-2,3-trans-3,4-cis-3,3',4',7-tetrahydroxy-4-<(2S,3S)-2,3-trans-3,3',4',7-tetrahydroxyflavan-6-yl>flavan 
• 127644-47-7 (2R,3S,4R,7S,8R)-2,8-Bis-(3,4-dihydroxy-phenyl)-4-(2,4-dihydroxy-phenyl)-3,4,7,8-tetrahydro-2H,6H-pyrano[3,2-g]chromene-3,7-diol 
• 127644-39-7 (+)-epifisetinidol-(4β,6)-(-)-fisetinidol 
• 127644-41-1 (4β,6)-bis-(+)-epifisetinidol 

Relevant academic research and scientific papers

Oligomeric Flavanoids. Part 10. Structure and Synthesis of the First Tetrahydropyranochromenes Related to (4,6)-Bis-(-)-fisetinidol Profisetinidins

The range of natural bis-fisetinidol profisetinidins is extended by identification of (+)-epifisetinidol-(4α,6)-(-)-fisetinidol (5), (4α,6)-bis-(+)-epifisetinidol (7), (4β,6')-bis-(-)-fisetinidol (13), and (-)-fisetinidol-(4β,6')-(+)-epifisetinidol (15).They are accompanied in the heartwood of Colophospermum mopane by the first tetrahydropyranochromenes (17), (19), (21), and (23), related to the (4,6)-bis-(-)-fisetinidol profisetinidins (1) and (2).Under mild basic conditions the latter compounds undergo pyran rearrangements affording tetrahydropyranochromenes (17), (19), (21), and (23) as well as two additional C-2(F) epimeric pairs (25), (27), and (29), (31).The same intermediate quinone-methide presumably leading to the c-ring-isomerized analogues may feasibly also explain the genesis of the variety of compounds in the mopane displaying a C-2-epimeric relationship to the predominant (-)-fisetinidol monomeric precursor.

Synthesis of Condensed Tannins. Part 4. A Direct Biomimetic Approach to - and -Biflavanoids

The generation of flavanyl-4-carbo-cations from flavan-3,4-diols and their condensation with nucleophilic flavan-3-ols to form - and -biflavanoids at ambient temperatures and mildly acidic aqueous conditions apparently simulates the initial step in condensed tannin formation in a number of natural sources.The stereospecificity (or stereoselectivity) of the reaction is conditioned mainly by the 2,3-cis or 2,3-trans stereochemistry of the parent flavan-3,4-diol, but also by the nuclephilicity of the flavan-3-ol, and its regiospecific (or regioselective) course by steric factors arising from variation in substitution of the receptive A-ring of the flavan-3-ol.