89385-96-6

Upstream product

• 100-39-0 benzyl bromide 
• 89386-27-6 (2R,3S)-3,5,7,3',4'-penta-O-benzyl-8-(2,2,2-trifluoroacetyl)flavan 
• 85443-49-8 (2R,3S)-3,5,7-tris(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)chroman 
• 154-23-4 catechin 
• 20728-73-8 5,7,3',4'-tetra-O-benzyl-(+)-catechin 
• 89385-18-2 3,5,7,3',4'-penta-O-benzyl-8-formylcatechin 

Downstream Products

• 1599460-38-4 bis(3,5,7,3',4'-penta-O-benzyl-8-catechinyl)methanone 

Relevant academic research and scientific papers

Total synthesis of (-)-bis-8,8′-catechinylmethane isolated from cocoa liquor

An efficient synthesis of bis-8,8′-catechinylmethane, a dimeric flavanol linked through a methylene bridge, is described. Our strategy involved a regioselective coupling via a trifluoroacetic anhydride condensation reaction followed by ketone reduction to the methylene employing new conditions (lithium aluminum hydride and hexafluorophosphoric acid).

Hydroxylation of ring A of flavan-3-ols: Influence of the ring A substitution pattern on the oxidative rearrangement of 6-hydroxyflavan-3-ols

A general procedure for the oxidation of catechin derivatives is described, leading to the introduction of a new hydroxyl group at C-6. This procedure has been used for the synthesis of a number of 6-hydroxy flavan-3-ols, including elephantorrhizol, a natural flavan-3-ol exhibiting a fully substituted A ring. The substitution at C-8, albeit of poor influence on the course of this oxidation reaction, has been demonstrated to be preponderant for the further spontaneous oxidation and rearrangement of 6-hydroxy-flavan-3-ols into p-benzoquinones. The whole procedure allows the preparation of 6-alkyl substituted benzoquinones derived from catechin. Georg Thieme Verlag Stuttgart.

Synthesis of modified proanthocyanidins: Introduction of acyl substituents at C-8 of catechin. Selective synthesis of a C-4 → O → C-3 ether-linked procyanidin-like dimer

The regioselective introduction of substituents at C-8 of (+)-catechin is described, leading to the synthesis of several catechin derivatives with various substitution patterns to be used for the further synthesis of modified proanthocyanidins. Thereafter, a new 3-O-4 ether-linked procyanidin-like derivative was synthesized. Its formation was selectively achieved through TiCl4-catalyzed condensation of 4-(2-hydroxyethoxy)tetra-O-benzyl catechin with the 8-trifluoroacetyl adduct of tetra-O-benzyl catechin.