中华医学超声杂志

应用化学 ›› 2010, Vol. 27 ›› Issue (07): 863-865.DOI: 10.3724/SP.J.1095.2010.90639

• 研究简报 • 上一篇    下一篇

光学纯(S)- 2-(苄氧酰氨基)-4-氧代丁酸苄酯的合成和结构表征

安莲英*,张振国,赵先银,雷宁,裴林芳   

  1. (成都理工大学材料与化学化工学院 成都 610059)
  • 收稿日期:2009-09-29 修回日期:2009-11-27 出版日期:2010-07-10 发布日期:2010-07-10
  • 通讯作者: 安莲英，女，博士，教授; E-mail:anliany@cdut.edu.cn; 研究方向：应用化学

Synthesis and Structural Characterization of Optical Pure (S)-Benzyl-2-(benzyloxycarbonylamino)-4-oxobutanoate

AN Lian-Ying*, ZHANG Zhen-Guo, ZHAO Xian-Yin, LEI Ning, PEI Ling-Fang   

  1. (College of Materials and Chemistry & Chemical Engineering,Chengdu University of Technology，Chengdu 610059)
  • Received:2009-09-29 Revised:2009-11-27 Published:2010-07-10 Online:2010-07-10

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摘要：

以L-蛋氨酸为起始原料，经甲基化、水解、羧基和氨基保护及氯铬酸吡啶嗡盐(PCC)氧化等6步反应，合成了高光学纯度的(S)-2-(苄氧酰氨基)-4-氧代丁酸苄酯。 通过1H NMR、IR、MS和mp测试技术表征了其结构；分别用手性柱HPLC和旋光仪法测定了它的化学纯度和光学纯度(ee%值)分别为99.3%和99.5%，产物的总收率为30.0%。

关键词: (S)-(苄氧酰氨基)-氧代丁酸苄酯, L-蛋氨酸, 合成

Abstract:

(S)-Benzyl-2-(benzyloxycarbonylamino)-4-oxobutanoate was synthesized from L-methionine via methylation reaction, hydrolysis, carboxyl and amino protection, pyridinium chorochromate(PCC) oxidation. The structure of the target product was characterized by means of 1H NMR, IR and MS. The optical purity was determined by HPLC and polarimeter method. The overall yield was 30.0%. The purity and ee value of the target compound were 99.3% and 99.5% respectively.

Key words: (S)-benzyl-(benzyloxycarbonylamino)-oxobutanoate, L-methionine, Synthesis

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