Polyhydroxylated Piperidines and Azepanes from D-Mannitol. Synthesis of 1-Deoxynojirimycin and Analogues

Article abstract of DOI:10.1016/S0040-4039(00)76888-2

D-mannitol and L-iditol bis-epoxides, easily obtained from D-mannitol, are convenient substrates for the synthesis of polyhydroxylated piperidines and azepanes, via a nucleophilic opening of one epoxy function followed by a spontaneous intramolecular ring closure.Using this strategy 1-deoxynojirimycin and analogues were prepared. - Key words: D-mannitol, Piperidine, Azepane, 1-deoxynojirimycin, 1,5-dideoxy-1,5-imino-L-gulitol, β-Glycosidase inhibitor.