Fmoc(S)2-氨基-2-甲基戊-4-烯酸的合成路线改进

Improved synthesis of 2-amino-2-methylpent-4-enoic acid

设计合成手性非天然氨基酸。制备了五元内酯环,亲电取代后得到差相异构体。通过重结晶得到单一构型的产物,经酸水解制备得到目标产物。结果得到的非天然氨基酸经1H NMR鉴定、旋光鉴定并与标准值比对。对于已有的氨基酸合成路线进行优化,以新戊醇氧化的方法制备新戊醛,合成路线稳定可靠并节约了成本,制备了(S)2-氨基-2-甲基戊-4-烯酸,产物的ee值为69.7%。

To synthesize a-methyl-a-amino acids,isomers were prepared through alkylation of prepared five-membered lactone ring.And then the product was prepared via hydrolysis and Fmoc protection.The product and important intermediates were analyzed by IN NMR and optical rotation identification.The results showed that the synthetic route was reliable and easy to operate,so it is suitable for large scale production of a-methyl-a-amino acids.