微波促进1,3-偶极环加成反应合成氮杂糖苷衍生物

高等学校化学学报 ›› 2010, Vol. 31 ›› Issue (9): 1791.

微波促进1,3-偶极环加成反应合成氮杂糖苷衍生物

李小六^1,2, 张宏波¹, 朱振刚¹, 陈华¹, 段科芳¹, 张平竹¹

1. 河北大学化学与环境科学学院, 河北省化学生物学实验室, 保定 071002;
2. 北京大学天然药物及仿生药物国家重点实验室, 北京 100191

收稿日期:2009-12-08 出版日期:2010-09-10 发布日期:2010-09-10
通讯作者: 李小六，男，博士，教授，博士生导师，主要从事糖类衍生物的设计、合成及生物活性研究. E-mail: lixl@hbu.cn
基金资助:
国家自然科学基金（批准号: 20672027, 20972039）、河北省自然科学基金（批准号: B2008000588）和北京大学天然药物及仿生药物国家重点实验室开放课题基金（批准号: 20080205）资助.

Efficient and Stereoselective Synthesis of Azasugar Derivatives Based on Microwave Assisted 1,3-Dipolar Cycloaddition

LI Xiao-Liu^1,2*, ZHANG Hong-Bo¹, ZHU Zheng-Gang¹, CHEN Hua¹, DUAN Ke-Fang¹, ZHANG Ping-Zhu¹

1. Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei Univeristy, Baoding 071002, China;
2. State Key Laboratory of Natural and Mimetic Drugs, Peking University, Beijing 100191, China

Received:2009-12-08 Online:2010-09-10 Published:2010-09-10
Contact: LI Xiao-Liu. E-mail: lixl@hbu.cn
Supported by:
国家自然科学基金（批准号: 20672027, 20972039）、河北省自然科学基金（批准号: B2008000588）和北京大学天然药物及仿生药物国家重点实验室开放课题基金（批准号: 20080205）资助.

摘要/Abstract

摘要： 利用微波促进氮杂糖硝酮(2)与丙烯酸类衍生物(3)发生1,3-偶极环加成反应, 立体选择性地得到了一系列新的含异噁唑烷的氮杂糖衍生物(4), 反应效率显著提高, 反应时间由95 h缩短为5~15 min, 收率由67%提高到78%~88%. 利用NMR和HRMS等方法结合化合物(4d-1)的单晶结构确定了产物的结构和相对构型.

关键词: 氮杂糖衍生物, 微波促进有机合成, 1,3-偶极环加成, 立体选择性

Abstract: In order to develop an efficient, practical and stereoselective method to access functionalized azasugar derivatives the microwave assisted 1,3-dipolar cycloaddition of azasugar nitrone and acrylates was investigated which afforded a series of novel azasugar derivatives containing an isoxazolindine moiety. The reaction was performed in a sealed microwave reactor at 110 ℃ in the solution of toluene and proceeded efficiently in yields up to 78%—88% within 5—15 min. The structures and configurations of the products were tentatively determined by ¹H NMR, ¹³C NMR, 2D NMR and HRMS spectral analyses with comparison to the reported X-ray single crystallographic structure of the product 4d-1.

Key words: Azasugar derivative, Microwave assisted organic synthesis, 1,3-Dipolar cycloaddition, Stereoselective

TrendMD:

李小六, 张宏波, 朱振刚, 陈华, 段科芳, 张平竹. 微波促进1,3-偶极环加成反应合成氮杂糖苷衍生物. 高等学校化学学报, 2010, 31(9): 1791.

LI Xiao-Liu*, ZHANG Hong-Bo, ZHU Zheng-Gang, CHEN Hua, DUAN Ke-Fang, .... Efficient and Stereoselective Synthesis of Azasugar Derivatives Based on Microwave Assisted 1,3-Dipolar Cycloaddition. Chem. J. Chinese Universities, 2010, 31(9): 1791.

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