A Simple Convergent Synthesis of the Mannosidase Inhibitor 1-Deoxymannonojirimycin from Sucrose

Article abstract of DOI:10.1016/0040-4039(92)88046-8

The glycosidase inhibitor 1-deoxymannonojirimycin (1,5-dideoxy-1,5-imino-D-mannitol) was synthesized in four simple steps from sucrose via 6,6'-diazido-6,6'-dideoxysucrose and 6-azido-6-deoxy-D-fructofuranose.The "isomeric ballast" of the sequence, 6-azido-6-deoxy-D-glucose, could be partially converted into 6-azido-6-deoxy-d-fructofuranose with the aid of glucose isomerase (E.C. 5.3.1.5) demonstrating a novel synthetic application of this enzyme.The sequence allows access to multigramm quantities of 1-deoxy-mannonojirimycin in over 30percent overall yield without the need for expensive reagents and protecting group manipulations.Key Words: 1-deoxymannonojirimycin, mannosidase inhibitor, glucose isomerase, sucrose, synthesis