微波促进立体选择性高效合成糖基α,β-不饱和酯类化合物

doi:10.6023/cjoc1201201

有机化学 ›› 2012, Vol. 32 ›› Issue (08): 1519-1525.DOI: 10.6023/cjoc1201201 上一篇下一篇

研究简报

微波促进立体选择性高效合成糖基α,β-不饱和酯类化合物

李小六, 王玮, 李锐, 张平竹, 陈华

河北大学化学与环境科学学院河北省化学生物学重点实验室保定 071002

收稿日期:2012-01-20 修回日期:2012-04-05 发布日期:2012-04-26
通讯作者: 李小六 E-mail:lixl@hbu.edu.cn
基金资助:
国家自然科学基金(Nos. 20972039, 21172051)、973计划前期专项(No. 2010CB534913)和河北省高等学校科学技术研究重点(No. ZH2011110)资助项目.

Efficient and Stereoselective Synthesis of Carbohydrate α,β-Un- saturated Esters by Microwave Assisted Wittig Reaction

Li Xiaoliu, Wang Wei, Li Rui, Zhang Pingzhu, Chen Hua

Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002

Received:2012-01-20 Revised:2012-04-05 Published:2012-04-26
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972039, 21172051), 973 Program (No. 2010CB534913) and the Natural Science Foundations of Education Department of Hebei Province (No. ZH2011110).

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摘要/Abstract

利用微波促进糖醛与叶立德(Ph₃P=CHCOOEt)发生Wittig反应, 立体选择性地合成了含有α,β-不饱和酯的糖烯类化合物, 反应效率显著提高, 使用不同的反应溶剂可实现对反应立体选择性的控制. 并通过¹H NMR中双键氢的偶合常数确定了产物的构型.

关键词: α,β-不饱和酯类, 糖类衍生物, 微波促进有机合成, 立体选择性Wittig反应

A stereoselectively controlled Wittig reaction of sugar aldehydes with Ph₃P=CHCOOEt under microwave radiation was investigated. The reaction was curried out effectively and stereoselectively depending upon the solvents used, providing a convenient access to the glycosyl α,β-unsaturated esters. The structures and configurations of the products were determined according to the NMR spectra and the coupling constants of the olifenic protons (CH=CH).

Key words: α,β-unsaturated ester, carbohydrate derivatives, microwave assisted reaction, stereoselective Wittig reaction

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李小六, 王玮, 李锐, 张平竹, 陈华. 微波促进立体选择性高效合成糖基α,β-不饱和酯类化合物[J]. 有机化学, 2012, 32(08): 1519-1525.

Li Xiaoliu, Wang Wei, Li Rui, Zhang Pingzhu, Chen Hua. Efficient and Stereoselective Synthesis of Carbohydrate α,β-Un- saturated Esters by Microwave Assisted Wittig Reaction[J]. Chin. J. Org. Chem., 2012, 32(08): 1519-1525.

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微波促进立体选择性高效合成糖基α,β-不饱和酯类化合物

Efficient and Stereoselective Synthesis of Carbohydrate α,β-Un- saturated Esters by Microwave Assisted Wittig Reaction

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