A Practical Synthesis of Various 2‐Deoxy‐<i>N</i>‐glycosides by Using <scp>D</scp>‐Glucal

Abstract

Abstract 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.