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

TitleAziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition
Publication TypeJournal Article
Year of Publication2005
AuthorsDhavale, DD, Kumar, KSA, Chaudhari, VD, Sharma, T, Sabharwal, SG, PrakashaReddy, J
JournalOrganic & Biomolecular Chemistry
Volume3
Issue20
Pagination3720-3726
Date PublishedOCT
Type of ArticleArticle
ISSN1477-0520
Abstract

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.

DOI10.1039/b509216g
Type of Journal (Indian or Foreign)

Foreign

Impact Factor (IF)

3.559

Divison category: 
Organic Chemistry