DIVERGENT GROWTH OF BRANCHED CARBAMATES: INTERMEDIATES FOR CONSTRUCTING MULTIVALENT PLATFORMS

David S. Jones*, Martina E. Tedder, Christina A. Gamino, Jeffrey R. Hammaker, Huong-Thu Ton-Nu

La Jolla Pharmaceutical Company
6455 Nancy Ridge Drive, San Diego, CA 92121
dave.jones@ljpc.com

Abstract

Multivalent active carbonate esters were prepared by a new method of divergent growth. Branching occurs by reacting 4-nitrophenylcarbonate esters with diethanol amine, or other N,N-dihydroxyalkyl amines, resulting in N,N-dihydroxyalkyl carbamate linkages. The resulting terminal hydroxyl groups were converted in-situ to 4-nitrophenylcarbonate esters which were conveniently isolated and purified. Each repetition of the process doubles the number of terminal carbonate esters, thus providing dendrimer-like branched structures of increased valency. Reaction with appropriately functionalized amine-containing compounds provides an entry into multivalent platform molecules for the preparation of multivalent bioconjugates.

Presented at the
221st ACS National Meeting
San Diego, CA
April 1-5, 200