Deoxysugar Synthesis. I. Lithium-ethylamine Reduction of Carbohydrate Phosphorodiamidates

Abstract

Following the procedure of Ireland, et al., 3-phosphorodiamidates (1b and 6b) of 1, 2 : 5, 6-di-O-isopropylidene-glucose and -allose were treated with lithium-ethylamine to give a 2, 3-dideoxy compound (3) in good yield, while similar treatment of a glucosaminide 3-phosphorodiamidate (11b) yielded a 3-deoxy derivative (12a). Thus, this method has the advantage of convenience for the preparation of deoxysugars.