糖基修饰的氨基酸类化合物的合成

Synthesis of Glycose-Containing Amino Acid Derivatives

通过对5种氨基酸酯化和氨基保护得到苄氧羰基氨基酸甲酯,经肼解制备苄氧羰基氨基酸酰肼,然后分别与3种不同的糖基异硫氰酸酯反应,制备了相应的目标化合物15个,且产率均在60%以上.所有新化合物均经元素分析,IR,MS和1HNMR确证.同时探索了苄氧羰基氨基酸甲酯肼解的最佳反应条件.

Fifteen target compounds were synthesized with the following three steps： amino acids were protected to form carbobenzoxyamino acid methyl esters, the carbobenzoxyamino acid methyl esters reacted with hydrazine to give carbobenzoxy amino acid hydrazides, and treatment of the carbobenzoxy amino acid hydrazides with glycosyl isothiocyanates afforded 3a-3o in 65%-86% yields. All the new compounds were characterized by elemental analysis, MS, IR and 1H NMR spectra. Besides, the optimal reaction condition of the hydrazinolysis of carbobenzoxyamino acid methyl esters was studied.