糖-アミノ酸結合体の研究 (第2報)

D-Glucose誘導体のN-Benzyloxycarbonylglycine Esterの合成について

抄録

In order to synthesize the glycine ester of D-glucose, attempt was made to obtain the starting material, 6-O-(N-benzyloxycarbonylglycyl)-D-glucopyranose, by esterification of N-benzyloxycarbonylglycine with glucose derivative and it was found that dicyclohexylcarbodiimide is a good condensation agent. Compared to the ester condensation of N-benzyloxycabonylglycine and glucose derivative with mixed anhydride of other acids, the use of dicyclohexylcarbodiimide as the condensation agent was found to have the advantage of not forming a large amount of by-products. Further, the latter reagent was found to have entirely no effect on the urethan bond like N-benzyloxycarbonyl group. This process was used to obtain N-benzyloxycarbonylglycine ester of four kinds of glucose derivatives whose hydroxyls other than that at 6-position were protected, and three of them easily afforded 6-O-(N-benzyloxycarbonylglycyl)-α-D-glucopyranose.