%0 Journal Article %J Organic & Biomolecular Chemistry %D 2005 %T Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition %A Dhavale, Dilip D. %A Kumar, K. S. A. %A Chaudhari, Vinod D. %A Sharma, T. %A Sabharwal, Sushma G. %A PrakashaReddy, J. %X

The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-alpha-D-xylo-5 -eno-heptofuranuronate 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.

%B Organic & Biomolecular Chemistry %I ROYAL SOC CHEMISTRY %C THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND %V 3 %P 3720-3726 %8 OCT %G eng %N 20 %9 Article %3

Foreign

%4 3.559 %R 10.1039/b509216g