Reviews

Application Progress of Silica Gel Supported Acids in Carbohydrate Chemistry

  • Yan Shiqiang ,
  • Zhang Wei ,
  • Ding Ning ,
  • Li Yingxia
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  • a School of Pharmacy, Fudan University, Shanghai 201203;
    b School of Pharmacy, Ocean University of China, Qingdao 266003

Received date: 2012-03-03

  Revised date: 2012-05-09

  Online published: 2012-06-01

Supported by

Project supported by the National Natural Science Foundation of China (Nos. 81072525, 21002014).

Abstract

Silica gel and its supported acids have been used widely in organic synthesis. Based on our researches, their applications in carbohydrate chemistry are reviewed mainly focusing on the glycosylation, functional group transformation, and hydrolysis applications.

Cite this article

Yan Shiqiang , Zhang Wei , Ding Ning , Li Yingxia . Application Progress of Silica Gel Supported Acids in Carbohydrate Chemistry[J]. Chinese Journal of Organic Chemistry, 2012 , 32(11) : 2081 -2089 . DOI: 10.6023/cjoc1203031

References

[1] Corma, A. Curr. Opin. Solid State Mater. Sci. 1997, (2), p. 63.

[2] Sikdar, S. K.; Howell, S. G. J. Cleaner Prod. 1998, 6, 253.

[3] Varma, R. S. Green Chem. 1999, 1, 43.

[4] Baghernejad, B. Mini-Rev. Org. Chem. 2011, 8, 91.

[5] Salehi, P.; Zolfigol, M. A.; Shirinic, F.; Baghbanzadeh, M. Curr. Org. Chem. 2006, 10, 2171.

[6] Rauter, A. P.; Xavier, N. M.; Lucas, S. D.; Santos, M. Adv. Carbohydr. Chem. Biochem. 2010, 63, 29.

[7] Fischer, E. Ber. Deutsch. Chem. Ges. 1893, 26, 2400.

[8] Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.

[9] Hanessian, S.; Lou, B. Chem. Rev. 2000, 100, 4443.

[10] Jensen, K. J. J. Chem. Soc., Perkin Trans. 1 2002, 2219.

[11] Toshima, K. Carbohydr. Res. 2006, 341, 1282.

[12] Toshima, K.; Sasaki, K. Comprehensive Glycoscience, Vol. 1, Amsterdam, Elsevier, 2007, p. 261.

[13] Matsushita, Y.; Sugamoto, K.; Kita, Y.; Matsui, T. Tetrahedron Lett. 1997, 38, 8709.

[14] Chakraborti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896.

[15] Agarwal, A.; Rani, S.; Vankar, Y. D. J. Org. Chem. 2004, 69, 6137.

[16] Misra, A. K.; Tiwari, P.; Agnihotri, G. Synthesis. 2005, 260.

[17] Tiwari, P.; Agnihotriand, G.; Misra, A. K. Carbohydr. Res. 2005, 340, 749.

[18] Colinas, P. A.; Nuńez, N. A.; Bravo, R. D. J. Carbohydr. Chem. 2008, 27: 141–147.

[19] Mukhopadhyay, B.; Collet, B.; Field, R. A. Tetrahedron Lett. 2005, 46, 5923.

[20] Mukherjee, C.; Misra, A. K. Synthesis 2007, 683.

[21] Mukhopadhyay, B.; Maurer, S. V.; Rudolph, N.; van Well, R. M.; Russell, D. A.; Field, R. A. J. Org. Chem. 2005, 70, 9059.
[22] Du, Y.; Wei, G.; Cheng, S.; Hua, Y.; Linhardt, R. J. Tetrahedron Lett. 2006, 47, 307.

[23] Ludek, O. R.; Gu, W.; Gildersleeve, J. C. Carbohydr. Res. 2010, 345, 2074.

[24] Agnihotri, G.; Misra, A. K. Carbohydr. Res. 2006, 341, 2420.

[25] Chun, Y. X.; Yan, S. Q.; Li, X. P.; Ding, N.; Zhang, W.; Wang, P.; Li, Y. X.; Li, M. Tetrahedron Lett. 2011, 52, 6196.

[26] Roy, B.; Mukhopadhyay, B. Tetrahedron Lett. 2007, 48, 3783.

[27] Shaikh, N.; Russo, L.; Cipolla, L.; Nicotra, F. Mol. Diversity 2011, 15, 341.

[28] Richel, A.; Laurent, P.; Wathelet, B.; Wathelet, J. P.; Paquot, M. Tetrahedron Lett. 2010, 51, 1356.

[29] Zhou, J. F.; Chen, X.; Wang, Q. B.; Zhang, B.; Zhang, L. Y.; Yusulf, A.; Wang, Z. F.; Zhang, J. B.; Tang, J. Chin. Chem. Lett. 2010, 21, 922.

[30] Dasgupta, S.; Pramanik, K.; Mukhopadhyay, B. Tetrahedron 2007, 63, 12310.

[31] Mandaland, S.; Mukhopadhyay, B. Tetrahedron 2007, 63, 11363.

[32] Rajput, V. K.; Mukhopadhyay, B. J. Org. Chem. 2008, 73, 6924.

[33] Roy, B.; Pramanik, K.; Mukhopadhyay, B. Glycoconjugate J. 2008, 25, 157.

[34] Dasgupta, S.; Mukhopadhyay, B. Eur. J. Org. Chem. 2008, 5770.

[35] Roy, B.; Field, R. A.; Mukhopadhyay, B. Carbohydr. Res. 2009, 344, 2311.

[36] Verma, P.; Mukhopadhyay, B. Carbohydr. Res. 2009, 344, 2554.

[37] Wu, Y.; Yu, J. G.; Ma, X. F.; Zhang, J. S. Chin. Chem. Lett. 2007, 18, 1173.

[38] Rodríguez, O. M.; Colinas, P. A.; Bravo, R. D. Synlett 2009, 1154.

[39] Kinfe, H. H.; Mebrahtu, F. M.; Sithole, K. Carbohydr. Res. 2011, 346, 2528.

[40] Misra, A. K.; Tiwari, P.; Madhusudan, S. K. Carbohydr. Res. 2005, 340, 325.

[41] Mukhopadhyay, B.; Russell, D. A.; Field, R. A. Carbohydr. Res. 2005, 340, 1075.

[42] Agarwal, A.; Vankar, Y. D. Carbohydr. Res. 2005, 340, 1661.

[43] Agnihotri, G.; Misra, A. K. Tetrahedron Lett. 2006, 47, 3653.

[44] Agnihotri, G.; Tiwari, P.; Misra, A. K. J. Carbohydr. Chem. 2006, 25, 491.

[45] Liu, H. X.; Wu, Q. P.; Shu, Y. N.; Chen, X.; Xi, X. D.; Du, T. J.; Zhang, Q. S. Carbohydr. Res. 2009, 344, 2342.

[46] Du, T. J.; Wu, Q. P.; Liu, H. X.; Chen, X.; Shu, Y. N.; Xi, X. D.; Zhang, Q. S.; Li, Y. Z. Tetrahedron 2011, 67, 1096.

[47] Wu, H.; Shen, Y.; Fan, L. Y.; Wan, Y.; Shi, D. Q. Tetrahedron 2006, 62, 7995.

[48] Mukhopadhyay, B. Tetrahedron Lett. 2006, 47, 4337.

[49] Rajput, V. K.; Mukhopadhyay, B. Tetrahedron Lett. 2006, 47, 5939.

[50] Rajput, V. K.; Roy, B.; Mukhopadhyay, B. Tetrahedron Lett. 2006, 47, 6987.

[51] Roy, B.; Verma, P.; Mukhopadhyay, B. Carbohydr. Res. 2009, 344, 145.

[52] Yan, S. Q.; Ding, N.; Zhang, W.; Wang, P.; Li, Y. X.; Li, M. Carbohydr. Res. 2012, 354, 6.

[53] Kumar, G. D. K.; Baskaran, S. J. Org. Chem. 2005, 70, 4520.

[54] Kumar, P. S.; Kumar, G. D. K.; Baskaran, S. Eur. J. Org. Chem. 2008, 6063.

[55] Yadav, J. S.; Raghavendra, S.; Satyanarayana, M.; Balanarsaiah, E. Synlett 2005, 2461.

[56] Das, B.; Mahender, G.; Kumar, V. S.; Chowdhury, N. Tetrahedron Lett. 2004, 45, 6709.

[57] Niu, Y.; Wang, N.; Cao, X.; Ye, X. S. Synlett 2007, 2116.

[58] Mahender, G.; Ramu, R.; Ramesh, C.; Das, B. Chem. Lett. 2003, 734.

[59] Tiwari, P.; Misra, A. K. Tetrahedron Lett. 2006, 47, 3573.

[60] Dasgupta, S.; Roy, B.; Mukhopadhyay, B. Carbohydr. Res. 2006, 341, 2708.
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