Synthesis of the antibiotic 1,5-dideoxy-1,5-imino-D-glucitol; concomitant formation of the D-mannitol analogue

Article abstract of DOI:10.1002/recl.19871061105

The easy accessible 1,2-O-isopropylidene-3-O-benzyl-α-D-glucofuranose was converted in six steps into 1,2-O-isopropylidene-3,6-di-O-benzyl-5-deoxy-5-azido-α-D-glucofuranose.The latter afforded, after acidolysis followed by hydrogenolysis, 1-deoxynojirimicine and a small quantity of 1-deoxymannonojirimicine.The antibiotic thus obtained had an inhibitory effect on the trimming of N-linked carbohydrates in IgM.