Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition
| Title | Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition |
| Publication Type | Journal Article |
| Year of Publication | 2005 |
| Authors | Dhavale, DD, Kumar, KSA, Chaudhari, VD, Sharma, T, Sabharwal, SG, PrakashaReddy, J |
| Journal | Organic & Biomolecular Chemistry |
| Volume | 3 |
| Issue | 20 |
| Pagination | 3720-3726 |
| Date Published | OCT |
| Type of Article | Article |
| ISSN | 1477-0520 |
| 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. |
| DOI | 10.1039/b509216g |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.559 |
Divison category:
Organic Chemistry