Synthesis of new amino sugar derivatives from keto-sugars of D-xylose.
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(2)CSNH(2). Higher carbon sugar 16 was accidentally prepared at room temperature from the keto-sugar in the presence of NH(2)CONH(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.
Ji
Xiao-Ming
XM
New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450052, PR China.
Mo
Juan
J
Liu
Hong-Min
HM
Sun
He-Ping
HP
D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry*; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D018360:Crystallography, X-Ray; D050111:Imino Sugars; D007661:Ketoses / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D014994:Xylose / Q000737:chemistry*
D000606:Amino Sugars; D050111:Imino Sugars; D007661:Ketoses; D014994:Xylose