65085-05-4

Upstream product

• 14613-67-3 (2R^*,3S^*,4R^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol 
• 6563-36-6 (2R^*,3S^*,4R^*)-flavan-3,4-diol 
• 67-56-1 methanol 
• 51196-02-2 5,7,3',4'-tetra-O-methylepicatechin 
• 490-46-0 (2R,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-1[2H]-benzopyran-3,5,7-triol 
• 13650-85-6 (+/-)-taxifolin 3-acetyl-5,7,3',4'-tetramethyl ether 

Downstream Products

• 14613-67-3 (2R^*,3S^*,4S^*)-5,7,3',4'-tetramethoxyflavan-3,4-diol 
• 69256-15-1 (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan 

Relevant academic research and scientific papers

Chemoselective C-4 aerobic oxidation of catechin derivatives catalyzed by the trametes villosa laccase/1-hydroxybenzotriazole system: Synthetic and mechanistic aspects

Catechin derivatives were oxidized in air in the presence of the Trametes villosa laccase/1-hydroxybenzotriazole (HBT) system in buffered water/1,4-dioxane as reactionmedium. The oxidation products, flavan- 3,4-diols and the corresponding C-4 ketones, are

Heterocycles. XXV. Sodium Borohydride Reduction of Flavanonols

Solvent effects on the stereochemistry in the sodium borohydride reduction of (+/-)-flavanonols have been examined.The effects observed for the (+/-)-flavanonols with 5-OMe in 2-propanol, dioxane and methanol are explainable by the differences between the steric interactions inherent in the product-like transition states A and B.It has been also found that 5-OAc peculiarly affects the stereochemistry in the reduction to produce the (+/-)-catechin-type compounds in a one-pot process.The solvent and temperature effects are examined using a model analogous to the above.

HETEROCYCLES. XIV. EFFICIENT STEREOCONTROLLED SYNTHESIS OF RACEMIC FLAVONOIDS

Stereocontrolled synthesis of the flavonoids (2, 4 and 5) is described.Racemic taxifolin (dihydroquercetin) (14) is synthesized by application of this method.

LEUCOCYANIDIN: SYNTHESIS AND PROPERTIES OF (2R,3S,4R)-(+)-3,4,5,7,3',4'-HEXAHYDROXYFLAVAN

An isomer of leucocyanidin, (2R,3S,4R)-(+)-3,4,5,7,3',4'-hexahydroxyflavan has been synthesized from (+)-taxifolin, isolated in its phenolic form, and characterized by 1H and 13C NMR, and formation of the 5,7,3',4'-tetramethyl ether.Leucocyanidin readily polymerizes in acid solution to form a procyanidin polymer of high MW. - Key Word Index: Leucocyanidin; flavan-3,4-diols; synthesis; polymerization; phytochemical significance.