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有机化学
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有机化学 ›› 1999, Vol. 19 ›› Issue (6): 630-635. 上一篇    下一篇

研究论文

含嘌呤、嘧啶类有机碱基的丁内酯的合成

黄慧;王志丹;陈庆华   

  1. 北京师范大学化学系.北京(100875)
  • 发布日期:1999-12-25

Synthesis of 5-[(1S)-endo]-bornyloxybutyrolactones bearing purine and pyrimidine bases

Huang Hui;Wang Zhidan;Chen Qinghua   

  1. Beijing Normal Univ., Dept of Chem..Beijing(100875)
  • Published:1999-12-25

被引次数

12 | 3

利用天然手性助剂(-)-冰片所制得的手性源5-[(1s)-(-)-冰片氧基-2(5H)-呋喃酮差向异构体3a+3b与具有生理活性的嘌呤、嘧啶类有机碱基进行不对称Michael加成反应,得到了嘌呤、嘧啶类丁内酯非对映体混合物5a～5e及-5'a～5'e。报道了它们的合成方法以及IR、UV、^1HNMR、^1^3CNMR、MS、元素分析等结构分析数据。其中5d+5'd通过优势结晶拆分法得到单一的光学活性化合物。

关键词: 嘧啶P, 曼尼希反应, 生理生化特性, 差向异构, 结构分析, 不对称反应, 内酯衍生物, 冰片, 呋喃酮P, 嘌呤P

The 5-[(1S)-endo]-bornyloxybutyrolactones bearing purine and pyrimidine bases were obtained via the Michael addition of purines or pyrimidines to the epimeric mixture, 5-[(1S)-endo]-bornyloxy-2(5H)- furanones (3a+3b), prepared from the natural abundant chiral auxiliaxy borneol and 5-hydroxy-2(5H)-furanone 2. The synthetic method was studied and the new compounds were identified on the basis of their analytical and spectroscopic, IR, UV, ^1H NMR, ^1^3C NMR, MS data.

Key words: EPIMERISM, FURANONE P, STRUCTURAL ANALYSIS, PHYSICOCHEMICAL CHARACTERISTICS, LACTONE DERIVATIVE, PURINE P, MANNICH REACTION, PYRIMIDINE P, BORNEOLUM SYNTHETICUM NAGI CAMPHORA

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