A stereodivergent approach to 1-deoxynojirimycin, 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives

A stereodivergent synthesis of N-alkylated 1-deoxygalactonojirimycin and 1-deoxymannojirimycin derivatives has been achieved from a protected 1-deoxynojirimycin intermediate having two free OH groups tactically positioned at C-2 and C-4. The inversion of configuration of the secondary alcohols was performed by way of a Swern oxidation followed by a highly diastereoselective reduction using NaBH4 or L-Selectride.