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

作　　者：夏亮 彭涛 张首国 王刚 温晓雪 刘曙晨 王林[1,2] XIA Liang;PENG Tao;ZHANG Shou-guo;WANG Gang;WEN Xiao-xue;LIU Shu-chen;WANG Lin(College of Life Science and Bio-engineering,Beijing University of Technology,Beijing 100124,China;Academy of Military Sciences PLA China,Beijing 100850,China)

机构地区：[1]北京工业大学生命科学与生物工程学院,北京100850 [2]军事科学院军事医学研究院生物组,北京100850

出　　处：《当代化工》2018年第11期2285-2287,2292,共4页Contemporary Chemical Industry

基　　金：国家自然科学基金,项目号:81273431,81072531,30770655,21272273和21102176

摘　　要：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.

关 键 词：手性合成 位阻效应 新戊醛 PCC氧化 一步法合成 

分 类 号：TQ031.2[化学工程]