A Practical Synthesis of Various 2-Deoxy-N-glycosides by Using D-Glucal

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. A series of 2‐deoxy‐2‐iodo‐N‐glycosides were prepared by using D‐glucal, N‐iodosuccinimide, trimethylsilylacetamide, urea, imidazole, pyrrolidinone, and benzotriazole in good to excellent yields. Removal of iodine from C‐2 of the newly generated 2‐deoxy‐2‐iodo‐N‐glycosides led to formation of various 2‐deoxy‐N‐glycosides.