Simple syntheses of glycofuranosylamines derived from D-xylose, D-mannose, and L-rhamnose, intermediates in the preparation of some N-glycofuranosyl uracils

Abstract

3,5-O-Isopropylidene-D-xylofuranosylamine, 2,3-O-isopropylidene-L-rhamnofuranosylamine, and 2,3:5,6-di-O-isopropylidene-D-mannofuranosylamine have been prepared in high yield as toluene-p-sulphonates by reaction of the corresponding pyranosylamines with acetone, 2,2-dimethoxypropane, and toluene-p-sulphonic acid; the glycofuranosylamines have been used to prepare pyrimidine nucleosides.