Synthesis of an eight carbon homologue of α-homomannojirimycin (cas 127995-29-3) via a bicyclic aminolactone

Add time:08/22/2019    Source:sciencedirect.com

A thermally induced intramolecular 1,3-dipolar cycloaddition of an azidoester and subsequent sodium cyanoborohydride reduction of the resulting bicyclic vinylogous urethane to give a bicyclic aminolactone allows access to an eight carbon homologue of α-homomannojirimycin which is a weak fucosidase inhibitor. Intermediates with both an α- and β-amino acid moiety are described and may be useful for incorporation of homopipecolic acids into novel peptide libraries.

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