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

Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (9): 1791.

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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.

Abstract

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

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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[J]. Chem. J. Chinese Universities, 2010, 31(9): 1791.

References

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

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