An alternative route to 2-deoxysugar and 2,3-unsaturated sugar derivatives via the corresponding 1-nitro-1-alkenes

An efficient method for the preparation of suitably O-protected 2-deoxysugar oximes starting from corresponding sugar 1-nitro-1-alkenes and using tin(II) chloride as a reducing agent is described. The prepared oximes were further transformed into either free 2-deoxysugars or 2-deoxysugar nitriles and acids. 2,3-Unsaturated sugar oximes were also prepared starting from O-acetylated sugar 1-nitroalkenes. The preparation of 2-deoxy-d-glucose is representative.