氨基葡萄糖脲氨基酸类衍生物的合成

The synthesis of ureido glucosamine amino acid derivates

目的设计简便高效的合成路线,合成新型糖脲类化合物。方法以D-氨基葡萄糖盐酸盐为原料,在乙酸酐的作用下合成1,3,4,6-四-O-乙酰基-α-D-氨基葡萄糖硫酸盐,然后与三光气在两相溶剂中反应形成异腈酸酯,再与苯丙氨酸甲酯、缬氨酸甲酯、亮氨酸甲酯、谷氨酸二甲酯等氨基酸甲酯反应,得到4种产物,并以质谱、1 H NMR及13 C NMR、高分辨质谱等检测手段对合成样品的结构进行了分析。结果合成的目标产物的收率≥65%(以氨基葡萄糖盐酸盐计),纯度≥96%,且仪器分析数据确证了4个新型化合物的结构。结论该方法能简便、温和、经济、高效地合成氨基葡萄糖脲氨基酸类衍生物。

Objective To create a convenient and efficient synthetic route to get new ureido sugars. Methods 1,3,4, 6-tetra-O-acetyl-a-I）-glucosamine sulfate was prepared by direct acetylation of D-glu- cosamine hydrochloride with acetic anhydride. Then it was transformed into the corresponding isocya- nate by using triphosgene as the isocyanation agent in an aqueous two-phase system. Subsequently new ureido sugars were efficiently synthesized by coupling the isocyanate with Phenylalanine methyl ester, Valine methyl ester, Leucine methyl ester, and Glutamic acid dimethyl ester. The structures of these new compounds were analyzed by MS,tH NMR, and 13 C NMR spectroscopy. Results The yield of deri- vates was more than 65~//oo and the purity was more than 96%. The structures of the new compounds were confirmed according to the data from instrumental analysis. Conclusion Ureido glucosamine amino acid derivates can be prepared by this method simply, mildly, economically, and efficiently.