Aziridine carboxylate from D-glucose: synthesis of polyhydroxylated piperidine, pyrrolidine alkaloids and study of their glycosidase inhibition |
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| Authors: | Dhavale Dilip D Kumar K S Ajish Chaudhari Vinod D Sharma Tarun Sabharwal Sushma G Prakashareddy J |
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| Affiliation: | Garware Research Centre, Department of Chemistry, University of Pune, Pune, 411 007, India. ddd@chem.unipune.ernet.in |
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| 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. |
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