SYNTHESES OF 1,5-DIDEOXY-1,5-IMINO-D-MANNITOL FROM D-MANNOSE AND D-GLUCOSE

Article abstract of DOI:10.1016/0040-4039(84)80058-1

Unambigous enantiospecific syntheses of 1,5-dideoxy-1,5-imino-D-mannitol (LU1, 1-deoxy-mannojirimycin) are reported (i) from D-mannose via hydrogenation of a 5-azido-5-deoxy mannose, and (ii) from D-glucose, in which the key step involves nucleophilic substitution of a trifluoromethanesulphonyl group from C-2 of D-glucose.