Halogenated d-xylono-δ-lactams: synthesis and enzyme inhibition study

• The Corey–Link reaction was exploited with 3-keto-d-gluco derived sugar.
• New C-3 halogenated d-xylono-δ-lactams were synthesized.
• The Schmidt–Boyer reaction was exploited for the synthesis of d-xylono-δ-lactams.
• Glycosidase inhibitory activity of halogenated d-xylono-δ-lactams was studied.

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.

Halogenated d-xylono-δ-lactams were synthesized from commercially available d-glucose by using Corey–Link reaction and intra molecular Schmidt reaction as key steps. The glycosidase inhibition activity and conformational analysis by 1H NMR of these compounds was studied.Figure optionsDownload as PowerPoint slide