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 degrees C. Two diastereomers were isolated ? the -mannose and -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--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.