盐酸L-肉碱和盐酸乙酰L-肉碱的合成  

Enantioselective Synthesis of L-Carnitine and Acetyl-L-carnitine Hydrochlorides

作　　者：程青芳[1,2] 许兴友[1,2] 李艳辉[1] 王建[1] 姚泳[3] 

机构地区：[1]淮海工学院化工系 [2]南京理工大学材料化学实验室南京210094 [3]江苏正大天晴药业股份有限公司

出　　处：《有机化学》2006年第7期946-949,共4页Chinese Journal of Organic Chemistry

基　　金：江苏省科技厅自然科学基金(No.BK2005045);江苏省教育厅高校自然科学计划(No.05KJD150024)资助项目.

摘　　要：L-肉碱(维生素BT)和乙酰L-肉碱是长链脂肪酸运输的载体,广泛用于医药、保健食品及饲料等行业.本工作介绍了一种化学不对称合成盐酸L-肉碱和盐酸乙酰L-肉碱的方法.以自制的手性噁唑硼烷为催化剂,将起始原料γ-氯乙酰乙酸乙酯不对称催化氢化还原成(R)-γ-氯-β-羟基丁酸乙酯,这一步的化学收率和光学收率都较高.然后将(R)-γ-氯-β-羟基丁酸乙酯转化为盐酸L-肉碱和盐酸乙酰L-肉碱.合成盐酸L-肉碱只需两步,总收率为68.3%,ee值可达94.6%;合成盐酸乙酰L-肉碱需三步,总收率为62.6%,ee值可达96.8%.还考察了反应温度、催化剂及还原剂的量等因素对γ-氯乙酰乙酸乙酯的不对称氢化还原的化学产率和光学收率的影响.The enantioselective synthesis of L-carnitine and acetyl-L-carnitine hydrochlorides was described. The asymmetric reduction of ethyl γ-chloroacetoacetate catalyzed by chiral oxazaborolidines enantioselectively gave ethyl R-3-hydroxy-4-chlorobutyrate in good yield and enantioselectivity. In following two steps, such an ester was converted into L-carnitine hydrochloride in 68.3% overall yield with 94.6% ee and acetyl-L-carnitine hydrochloride in 62.6% overall yield with 96.8% ee. Some factors effecting the yield and the enantioselectivity of asymmetric reduction of ethyl γ-chloroacetoacetate were investigated.

关 键 词：盐酸L-肉碱 乙酰L-肉碱 手性嗯唑硼烷 不对称还原 

分 类 号：O621.25[理学—有机化学]