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Chinese Journal of Organic Chemistry >

2012 , Vol. 32 >Issue 08: 1519 - 1525

DOI: https://doi.org/10.6023/cjoc1201201

Notes

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

Received date: 2012-01-20

  Revised date: 2012-04-05

  Online 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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Abstract

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

Cite this article

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]. Chinese Journal of Organic Chemistry, 2012 , 32(08) : 1519 -1525 . DOI: 10.6023/cjoc1201201

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