SIOC English
有机化学
高级检索

有机化学 >

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

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

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
展开
  • 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

  网络出版日期: 2012-04-26

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.

收起

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
Expand
  • 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).

Fold

摘要

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

本文引用格式

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 . DOI: 10.6023/cjoc1201201

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

参考文献

[1] Franck, R. W.; Subramaniam, C. S.; John, T. V.; Blount, J. F. Tetrahedron Lett. 1984, 25, 2439.

[2] Giannis, A.; Sandhoff, K. Carbohydr. Res. 1987, 171, 201.

[3] Secrist III, J. A.; Wu, S.-R. J. Org. Chem. 1979, 44, 1434.

[4] Brimacombe, J. S.; McDonald, G.; Rahman, M. A. Carbohydr. Res. 1990, 205, 422.

[5] Kiddle, J. J. Tetrahedron 2000, 41, 1339.

[6] Postema, M. H. D.; Calimente, D.; Liu, L.; Behrmann, T. L. J. Org. Chem. 2000, 65, 6061.

[7] Yadav, J. S.; Prathap, I.; Tadi, B. Tetrahedron Lett. 2006, 47, 3773.

[8] Fleet, G. W. J.; Seymour, L. C. Tetrahedron Lett. 1987, 28, 3015.

[9] Corey, E. J.; Clark, D. A.; Goto, G.; Marfat, A.; Mioskowski, C.; Samuelsson, B.; Hlimmarstrom, S. J. Am. Chem. Soc. 1980, 102, 1436.

[10] Coumbarides, G. S.; Majid, M.; Muse, W. A.; Wyatt, P. B. J. Org. Chem. 2006, 71, 7888.

[11] Rokach, J.; Lau, C.-K.; Zamboni, R.; Guindon, Y. Tetrahedron Lett. 1981, 22, 2763.

[12] Vidal, S. B.; Garcia, M.; Montero, J. L.; Morere, A. Bioorg. Med. Chem. 2002, 10, 4051.

[13] Dunlap, N. K.; Mergo, W.; Jones, J. M.; Carrick, J. D. Tetrahedron Lett. 2002, 43, 3923.

[14] Srihari, P.; Kumar, P. B.; Subbarayudu, K.; Yadav, J. S. Tetrahedron Lett. 2007, 48, 6977.

[15] Dhavale, D. D.; Jachak, S. M.; Karche, N. P.; Trombini, C. Tetrahedron 2004, 60, 3009.

[16] Prakash, K. R. C.; Prahlada, S. R. Tetrahedron Lett. 1991, 32, 7473.

[17] Valverde, S.; Martin-Lomas, M.; Herradon, B.; Garcia-Ochoa, S. Tetrahedron 1987, 43, 1895.

[18] Jam, F.; Tullberg, M.; Luthman, K.; Gr?tli, M. Tetrahedron 2007, 63, 9881

[19] Schirok, H. J. Org. Chem. 2006, 71, 5538.

[20] G?rmer, K.; Waldmann, H.; Triola, G. J. Org. Chem. 2010, 75, 1811.

[21] Sun, Y.-R.; Li, Y.-P.; Zao, X.-M.; Liu, C.-J.; Wang, J.-D. Chin. J. Chem. 2008, 28, 1989 (in Chinese).(孙燕荣,李燕萍,糟新民,刘晨江,王吉德,有机化学,2008, 28, 1989.)

[22] Bian, Y.-J.; Hu, C.-X. Chin. J. Chem. 2011, 31, 1695 (in Chinese). (边延江,胡春祥,有机化学,2011, 31, 1695.)

[23] Das, S. K.; Reddy, K. A.; Rao, K. V. L. N.; Mukkanti, K. Carbohydr. Res. 2005, 340, 1387.

[24] Nadège, F.; Laetitia, D.; José, K.; Eric, G. Carbohydr. Res. 2008, 343, 2819.

[25] Li, X.-L.; Zhang, H.-B.; Zhu, Z.-G.; Chen, H.; Duan, K.-F.; Zhang, P.-Z. Chem. J. Chin. Univ. 2010, 31, 1791 (in Chinese).(李小六, 张宏波, 朱振刚, 陈华, 段科芳, 张平竹, 高等学校化学学报, 2010, 31, 1791.)

[26] Wang, W.; Li, X.-L.; Li, R.; Zhang, P.-Z.; Chen, H. Chem. J. Chin. Univ. 2012, 33, 958 (in Chinese).(王玮, 李小六, 李锐, 张平竹, 陈华, 高等学校化学学报, 2012, 33, 958.)

[27] Wolfrom, M. L.; Hanessian, S. J. Org. Chem. 1962, 27, 1800.

[28] Rajnikanth, B.; Seshadri, R. Tetrahedron Lett. 1989, 30, 755.

[29] Daly, S. M.; Armstrong, R. W. Tetrahedron Lett. 1989, 30, 5713.

[30] Seraffn, V.; Manuel, M. L.; Bernardo, H.; Silvestre, G. O. Tetrahedron 1987, 43, 1895.
Options
文章导航

/

〈 〉