Revision of the structures of partially acylated derivatives of aldose diethyl dithioacetals

Abstract

1H nuclear magnetic resonance spectroscopy is used to correct the structures of most of the known partially acylated derivatives of aldose diethyl dithioacetals which contain more than one acyl group. Previous work had suggested that the hydroxyl group on carbon-2 was the least readily acylated secondary hydroxyl group; current work indicates that it is among the most readily acylated. Evidence is presented which shows that the preferential methylation of aldose diethyl dithioacetals at O-2 is caused by the presence of the sulfur atoms.