Dhavale, Dilip D. ; Ajish Kumar, K. S. ; Chaudhari, Vinod D. ; Sharma, Tarun ; Sabharwal, Sushma G. ; PrakashaReddy, J. (2005) Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition Organic & Biomolecular Chemistry, 3 (20). pp. 3720-3726. ISSN 1477-0520
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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/2005...
Related URL: http://dx.doi.org/10.1039/B509216G
Abstract
The D-glucose derived aziridine carboxylate 5 was obtained from (E)-ethyl-6-bromo-1,2-O-isopropylidene-3-O-benzyl-5-deoxy-α-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 α-hydroxy-β-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.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Royal Society of Chemistry. |
| ID Code: | 75342 |
| Deposited On: | 22 Dec 2011 13:12 |
| Last Modified: | 22 Dec 2011 13:12 |
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