有机化学 ›› 2008, Vol. 28 ›› Issue (10): 1750-1755. 上一篇    下一篇

研究论文

微波促进的葡萄糖烯与硝酮的1,3-偶极环加成反应

李小六*; 王彦坡; 陈 华 ; 李志伟; 邢春勇   

  1. (河北大学化学与环境科学学院 化学生物学实验室 保定 071002)
  • 收稿日期:2008-02-02 修回日期:2008-03-24 发布日期:2008-10-20
  • 通讯作者: 李小六

Microwave Assisted 1,3-Dipolar Cycloaddition Reaction of exo-Glucal with Nitrone

LI, Xiao-Liu* ; WANG, Yan-Po; CHEN, Hua; LI, Zhi-Wei; XING, Chun-Yong   

  1. (Laboratory of Chemical Biology, College of Chemistry and Environmental Sciences, Hebei University, Baoding 071002)
  • Received:2008-02-02 Revised:2008-03-24 Published:2008-10-20
  • Contact: LI, Xiao-Liu

在微波辐射下, 葡萄糖烯(1)与硝酮2环加成反应的效率大大提到, 在乙二醇二甲醚溶液中, 200 ℃封管反应2 min, 环加成反应产物的收率可高达96%, 而且反应的立体选择性无明显变化. 利用环加成产物可进一步合成各种含官能团的碳糖苷衍生物, 找到了一种合成碳糖苷衍生物中间体的简便有效方法.

关键词: 微波促进, 螺异噁唑烷糖苷, 1,3-偶极环加成反应, 硝酮, 外糖烯

With microwave irradiation, the efficiency of the 1,3-dipolar cycloaddition of exo-glucal (1) with nitrones 2 was remarkably improved, and the yield of the microwave assisted reaction in a seamless pressure vial at 200 ℃ for 2 min could be up to 96%, providing a practical and convenient method for preparing spiro-isoxazolidine glycosides which are very important intermediates for synthesizing various C-glycosides possessing functional groups.

Key words: 1,3-dipolar cycloaddition, microwave assisted, exo-glycal, spiro-isoxazolidine glycoside, nitrone