Synthesis of new amino sugar derivatives from keto-sugars of d-xylose

Abstract

Several amino sugars and imino sugar derivatives were synthesized from keto-sugars of d-xylose through a series of reactions such as the Henry reaction, hydrogenation reactions, and nucleophilic addition reactions or substitution reactions. Thiazine derivative 15 was obtained by the reaction of the keto-sugar with NH 2CSNH 2. Higher carbon sugar 16 was accidentally prepared at room temperature from the keto-sugar in the presence of NH 2CONH 2. The structures of the compounds were confirmed by spectral analysis. The absolute configurations of all asymmetric carbon atoms of 6 and 8 were confirmed by X-ray crystallographic analysis.