We herein report the synthesis of 2‐deoxy‐2‐iodo‐glycosylamides, glycosylurea, N‐glycosylbenzotriazole, and N‐glycosyl imidazole by addition reaction of trimethylsilyl amides, imidazoles, and benzotriazoles to D‐glucal in the presence of N‐iodosuccinimide and propionitrile at 0 °C. Two diastereomers were isolated ― the α‐mannose and β‐gluco isomers. Reduction and substitution reaction of the iodine at position C‐2 led to formation of various 2‐deoxy‐N‐glycosides and 2‐hydroxy‐β‐D‐glucopyranosylamide. The newly generated compounds were screened for their inhibitory activity against various enzymes that included Nav1.7 sodium ion voltage‐gated channel in HEK293 cells and the results are discussed.

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