The use of sodium chlorite in the non-racemic synthesis of a potent inhibitor of glycolipid biosynthesis

Abstract

A facile and environmentally friendly synthesis of both enantiomers of a biologically important 1-N-iminosugar (azasugar) is presented. To this end, the use of a very cheap and non-toxic reagent, such as sodium chlorite, is featured in two key reactions. Additionally, a highly stereoselective epoxidation with dimethyloxirane (DMDO), and regioselective acid-catalyzed epoxide ring opening are also two environmentally friendly reactions that are employed in this synthesis. For all the above-mentioned, and also taking into account that protecting groups were not employed, we would like to present this synthetic route as an efficient approach for the development of environmental and sustainable syntheses of highly oxygenated biologically important compounds.