Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors Original Research Article

Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino-d-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-d-ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination.