高等学校化学学报

高等学校化学学报 ›› 1992, Vol. 13 ›› Issue (5): 617.

• 论文 • 上一篇    下一篇

碳苷合成研究——3-β-D-吡喃木糖基-1,2,4-氧杂二唑类化合物的合成

董领娇, 李莉, 马灵台, 张礼和   

  1. 北京医科大学药学院, 北京, 100083
  • 收稿日期:1991-07-27 出版日期:1992-05-24 发布日期:1992-05-24
  • 通讯作者: 张礼和
  • 基金资助:

    国家自然科学基金

Studies on the Synthesis of C-Nucleosides--Synthesis of 3-β-D-XyIopyranosyl-1,2,4-Oxadiazoles

DONG Ling-jiao, LI Li, MA Ling-tai, ZHANG Li-he   

  1. School of Pharmaceutical Sciences, Beijing Medical University, Beijing, 100083
  • Received:1991-07-27 Online:1992-05-24 Published:1992-05-24

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摘要： 本文研究了1-(2,3,4-三-O-苯甲酰-β-D-吡喃木糖基)-偕氨基肟与酸酐及酰氯的缩合反应,探讨了不同缩合剂、不同取代基对环合反应的影响,与酸酐反应可以一步完成,且收率较好;与酰氯反应分两步进行,第一步酰化,第二步脱水环合,芳环上取代基的电性效应,决定环合反应的难易,并证明了该环系的碳苷对酸、碱、热具有化学稳定性,本文合成了12个氧杂二唑类木糖碳苷及2个木糖基化的开环产物,通过光谱及元素分析,确定了它们的结构。

关键词: 1, 2, 4-氧杂二唑, 木糖碳苷, 缩合反应

Abstract: Fourteen new derivatives of 3-β-D-xylopyranosyl 1,2,4-oxadiazole were synthesized via condensating protected β-D-xylopyranosyl amidoxime with anhydrides or various substituted benzoyl chlorides in good yields.The 1,2,4-oxadiazole ring was formed directly by condensation of xylopyranosyl amidoxime and various anhydrides, but if the condensation occured by using substituted benzoyl chloride instead of anhydride, the cyclization was completed by two steps.The mechanism was discussed, 3-β-.D-xylopyranosyl-1,2,4-oxadiazole is stable under the condition of 1 mol/L HCl, 1 mol/L NaOH or at high temperature.

Key words: 1,2,4-Oxadiazole, Xylosyi C-nucleoside, Condensation reaction

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