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Design and synthesis of N–acetylglucosamine derived 5a-carbasugar analogues as glycosidase inhibitors
Narayana C., Kumari P., Ide D., Hoshino N., Kato A., Sagar R.
Published in Elsevier Ltd
Volume: 74
Issue: 15
Pages: 1957 - 1964
An efficient synthesis of new six-membered carbasugars in both L-form and D-form starting from N–acetylglucosamine is described. The key synthetic steps involved regioselective protection and deprotection, Ferrier carbocyclization, Peterson olefination, hydroboration and stereoselective epoxidation followed by regioselective epoxide ring opening reactions. These six-membered carbasugars showed moderate glycosidase inhibitory activity and one of the compounds was found selective towards β-galactosidase inhibitory activity. © 2018 Elsevier Ltd
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Published in Elsevier Ltd
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