Aziridine carboxylate from D-glucose:synthesis of polyhydroxylated piperidine,pyrrolidine alkaloids and study of their glycosidase inhibition

摘要

The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-l,2-O-isopropylidene-3-O-benzyl-5-deoxy-alpha-D-xylo-5-eno-heptofurariuronate 4 through conjugate addition of benzylamine and in situ intramolecular nucleophilic expulsion of bromine.The regioselective aziridine ring-opening,using water as a nucleophile,resulted in the alpha-hydroxy-beta-aminoester 6,which was exploited in the synthesis of six and five membered azasugars 1b/1c and 2b/2c,respectively.The glycosidase inhibitory activity of the title compounds was evaluated.