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Updated: Apr 19, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Halogenated D-xylono-δ-lactams: synthesis and enzyme inhibition study
Naresh Bhuma1, Madhuri Vangala1, Roopa J Nair2
1Department of Chemistry, Garware Research Centre, University of Pune, Pune 411007, India.
Abstract:
A concise synthesis of four C-3 fluoro/chloro-D-xylono-δ-lactams 3/4 has been reported. The methodology involves Corey-Link approach with suitably protected 3-oxo-D-gluco-furanose to introduce F/Cl as well as ester/amide functionalities at C-3 of glucose. In next steps, 5,6-O-isopropylidene group was converted to the 5-azido xylosugars that on opening of 1,2-acetonide group, and intramolecular Schmidt-Boyer reaction with TFA/H2O, in one pot, afforded lactams 3/4. Conformational aspect of δ-lactams was studied by the 1H NMR spectroscopy. The halogenated δ-lactams 3/4 showed no inhibition against different glycosidase enzymes.
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