Journal
TETRAHEDRON
Volume 57, Issue 22, Pages 4759-4766Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00399-4
Keywords
pentosidine; an advanced glycation end product; asymmetric alkylation; imidazo[4,5-b]pyridine; quaternization
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The chemical synthesis of pentosidine (1), an advanced glycation end product, was achieved via the asymmetric alkylation of the chiral schiff base derived from (+)-2-hydroxy-3-pinanone ((+)-HyPN) and glycine tert-butyl ester, the mercury salt mediated intramolecular guanylation, and the regioselective alkylation of imidazo[4,5-b]pyridine ring. This reliable synthetic achievement will promise availability of pentosidine (1) in quantities. (C) 2001 Elsevier Science Ltd. All rights reserved.
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