Synthetic methods for preparing procyanidin oligomers

Details Synthetic methods for preparing procyanidin oligomers Synthetic methods for preparing procyanidin oligomers

C - Chemistry, Metallurgy

07

D

C07D 311/32 (2006.01)

Patent

CA 2369799

Processes are disclosed for the production of linear and branched procyanidin oligomers having "n" procyanidin monomeric units where n is 2 to 18. The processes include coupling protected, activated monomers with an unprotected monomer to produce a partially protected (4~8) dimer. The dimer is optionally blocked, coupled with an activated protected monomer to produce a partially protected, optionally blocked trimer, and deprotected. The steps can be repeated to produce higher oligomers. Processes are also provided for producing (8~8), (8~6), and (6~6) dimers and doubly branched oligomers. Crystalline 8-bromo tetra-O-benzyl (-)-epicatechin is produced under certain conditions.

L'invention concerne des procédés de production d'oligomères de procyanidine linéaires et ramifiés ayant "n" unités monomères de procyanidine, n étant compris entre 2 et 18. Ces procédés consistent à coupler des monomères protégés activés avec un monomère non protégé pour obtenir un dimère partiellement protégé (4~8). Le dimère est éventuellement bloqué, couplé à un monomère protégé activé pour produire un trimère éventuellement bloqué, partiellement protégé et déprotégé. Les étapes peuvent être répétées pour obtenir des oligomères supérieurs. L'invention concerne également des procédés de production de dimères et oligomères ramifiés doubles (8~8), (8~6) et (6~6). La 8-bromo tetra-O-benzyl (-)-épicatéchine cristalline est obtenue sous certaines conditions.

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