Ptactical Synthesis of Nojirimycin

Abstract

The short step and efficient synthesis of nojirimycin (1) from commercially available 1,2-isopropylidene-D-glucofuranose (2) was described. Oxidation of 2 with (Bu3Sn)2O-Br2 followed by oximation, isomerization, and stereoselective reduction gave the 5-amino derivative of glucoconfiguration (6a), which was converted to nojirimycin bisulfite adduct (8) in 50% overall isolated yield.