Synthetic methods for preparing procyanidin oligomers

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

2005-03-08

2005-03-08

Nutter, Nathan M. (Department: 1711)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S355000, C549S399000

Reexamination Certificate

active

06864377

ABSTRACT:
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.

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