Simple syntheses of 4-O-glucosylated 1-deoxynojirimycins from maltose and cellobiose

Glucosidase inhibitors α-d-glucopyranosyl-(1→4)-1-deoxynojirimycin and β-d-glucopyranosyl-(1→4)-1-deoxynojirimycin were prepared from maltose and cellobiose, respectively, via the corresponding 5,6-eno derivatives, their epoxidation and the subsequent double reductive amination of the resulting 5-uloses. In both cases, the reported route is the first chemical synthesis not based on enzymatic glucosyl transfer.