Mars, Incorporated

Amit Basak

Craig Arthur Townsend

Leo J Romanczyk

Leo J Romancyzk, Jr

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&#x2192;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&#x2192;8), (8&#x2192;6), and (6&#x2192;6) dimers and doubly branched oligomers. Crystalline 8-bromo tetra-O-benzyl (&#x2212;)-epicatechin is produced under certain conditions.

Synthetic methods for preparing procyanidin oligomers

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&#x2192;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&#x2192;8), (8&#x2192;6), and (6&#x2192;6) dimers and doubly branched oligomers. Crystalline 8-bromo-tetra-O-benzyl-(&#x2212;)-epicatechin is produced under certain conditions.

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Baltimore, MD, United States of America

Amit Basak