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盐酸L-肉碱和盐酸乙酰L-肉碱的合成
引用本文:程青芳,许兴友,李艳辉,王建,姚泳. 盐酸L-肉碱和盐酸乙酰L-肉碱的合成[J]. 有机化学, 2006, 26(7): 950-953
作者姓名:程青芳  许兴友  李艳辉  王建  姚泳
作者单位:1. 淮海工学院化工系,连云港,222005;南京理工大学材料化学实验室,南京,210094
2. 淮海工学院化工系,连云港,222005
3. 江苏正大天晴药业股份有限公司,连云港,222006
基金项目:江苏省科技厅自然科学基金,江苏省教育厅资助项目
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.

关 键 词:盐酸L-肉碱  乙酰L-肉碱  手性噁唑硼烷  不对称还原
收稿时间:2005-05-12
修稿时间:2006-01-17

Enantioselective Synthesis of L-Carnitine and Ace-tyl-L-carnitine Hydrochlorides
CHENG Qing-Fang,XU Xing-You,LI Yan-Hui,WANG Jian,YAO Yong. Enantioselective Synthesis of L-Carnitine and Ace-tyl-L-carnitine Hydrochlorides[J]. Chinese Journal of Organic Chemistry, 2006, 26(7): 950-953
Authors:CHENG Qing-Fang  XU Xing-You  LI Yan-Hui  WANG Jian  YAO Yong
Affiliation:Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, Beijing 100850
Abstract:A new pulse sequence is proposed for extracting subspectra of individual components of sugar chains. The method uses a combination of the MMDY composite pulse and the double pulsed field gradient spin-echo and is shown to be useful in the analysis of complex spectra with many overlapped signals. The main advantages of this method are: (i) a significant decrease in experiment acquisition times; (ii) the mag- netization transfer is especially efficient, for example, for sugar residues such as Ara and Rha, which have one of the coupling of ca. 1 Hz around the sugar rings, complete subspectra can be quickly obtained; (iii) high-quality pure-absorption phase subspectra can be recorded without the use of the Z-filter technique; (iv) since the gradients merely serve to suppress unwanted signals, they are not subject to the sensitivity losses associated with gradient coherence pathway selection. Its application to the separation of severely overlap- ping spin systems is illustrated using glycoside sample.
Keywords:structural determination of oligosaccharide chain  MMDY composite pulse  NMR
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