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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (06): 768-771. 上一篇    下一篇

研究论文

(S)-6-苄氧基-5-羟基-3-氧代-己酸叔丁酯合成新方法

徐刚，孙丰来，吴坚平，杨立荣*   

  1. (浙江大学材料与化工学院 杭州 310027)
  • 收稿日期:2006-12-15 修回日期:2007-04-07 发布日期:2007-05-21
  • 通讯作者: 杨立荣

A New Way to Synthesis of (S)-tert-Butyl 6-Benzyloxy-5-hydroxy-3-oxohexanoate

XU Gang, SUN Feng-Lai, WU Jian-Ping, YANG Li-Rong*   

  1. (College of Material and Chemical Engineering, Zhejiang University, Hangzhou 310027)
  • Received:2006-12-15 Revised:2007-04-07 Published:2007-05-21
  • Contact: YANG Li-Rong

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研究了一条新的路线用于(S)-6-苄氧基-5-羟基-3-氧代-己酸叔丁酯的合成. 以廉价、易得的R-环氧氯丙烷为起始原料, 经过几步比较温和的反应得到目标化合物. 在此基础上, 通过对催化剂三氟化硼乙醚用量的考察以及两条反应路线优缺点的比较, 找到了一条适合大规模制备的工艺路线. 该路线具有收率高、原料易得、反应条件温和、产物容易分离、提纯等特点.

关键词: (S)-1-苯甲氧基-2,3-环氧丙烷, R-环氧氯丙烷, (R)-1-苄氧基-3-氯-2-丙醇, (S)-3-羟基-4-苄氧基丁腈, (S)-6-苄氧基-5-羟基-3-氧代-己酸叔丁酯

A new way to synthesis of (S)-tert-butyl 6-benzyloxy-5-hydroxy-3-oxohexanoate was investigated. The target compound was successfully prepared via several mildly reaction processes by using R-epichlorohydrin, which is an inexpensive and easily available starting material. Through screening the amounts of BF3•Et2O and comparing two different synthetic methods, this route becomes more suitable for large-scale preparation for its high yields, mildly reacting-conditions, easily available materials and facilely purification of products.

Key words: R-epichlorohydrin, (S)-1-benzyloxy-2,3-epoxypropane, (R)-3-chloro-1- benzyloxy-2-propanol, (S)-4-benzyloxy-3-hydroxybutanenitrile, (S)-tert-butyl 6-benzyloxy-5-hydroxy-3-oxohexanoate