Microwave-assisted conversion of carbohydrates. State of the art and outlook

Comptes Rendus Chimie

Volumn 14, Issue 2-3, 2011, Pages 224-234

  Richel, Aurore ^a   Laurent, Pascal ^a   Wathelet, Bernard ^a   Wathelet, Jean Paul ^a   Paquot, Michel ^a  

^a UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

Carbohydrates; Microwaves

Indexed keywords

EID: 79951957159     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2010.04.004     Document Type: Short Survey

References (83)

1. R. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge, and J. Roussel Tetrahedron Lett. 27 1986 279
2. R.J. Giguere, T.L. Bray, S.M. Duncan, and G. Majetich Tetrahedron Lett. 27 1986 4945
3. C.O. Kappe Angew. Chem. Int. Ed. 43 2004 6250
4. S. Caddick, and R. Fitzmaurice Tetrahedron 65 2009 3325
5. G. Descotes, and Y. Queneau W. Praznik, A. Huber, Carbohydrates as Organic Raw Materials IV 1998 WUV Wien 39
6. A. Corsaro, U. Chiacchio, V. Pistar, and G. Romeo Curr. Org. Chem. 8 2004 511 and references therein
7. A. Corsaro, U. Chiacchio, V. Pistar, and G. Romeo A. Loupy, Microwaves in Organic Synthesis 2nd Edition 2006 WILEY-VCH 579
8. E.A. Cioffi Curr. Top. Med. Chem. 8 2 2008 152
9. R.F. Helm, J. Ralph, and L. Anderson Org. Chem. 56 1991 7015
10. M. Csiba, J. Clophax, A. Petit, and S.D. Gero Tetrahedron Lett. 34 1993 1787
11. J. Clophax, L. Liagre, A. Loupy, and A. Petit Org. Process Res. Dev. 4 2000 498
12. S.K. Das, K.A. Reddy, V.L.N.R. Krovvidi, and K. Mukkanti Carbohydr. Res. 340 2005 1387
13. E. Soderberg, J. Westman, and S. Oscarson J. Carbohydr. Chem. 20 2001 397
14. P. Salanski, G. Descotes, A. Bouchu, and Y. Queneau J. Carbohydr. Chem. 17 1998 129
15. R.S. Varma, M. Varma, and A.K. Chatterjee J. Chem. Soc., Perkin Trans. 1 1993 999
16. S.V. Ley, and D.M. Mynett Synlett 1993 793
17. C. Limousin, J. Clophax, A. Petit, A. Loupy, and G. Lukacs J. Carbohydr. Chem. 16 1997 327
18. L.F. Bornaghi, and S.A. Poulsen Tetrahedron Lett. 46 2005 3485
19. N. Ferlin, L. Duchet, J. Kovensky, and E. Grand Carbohydr. Res. 343 2008 2819
20. R.R. Schmidt Angew. Chem. Int. Ed. 25 2003 212
21. R.F.D. Jones, P. Camilleri, A.J. Kirby, and G.N. Okafo J. Chem. Soc., Chem. Commun. 1994 1311
22. C. Stubenrauch Curr. Opin. Colloid Interface Sci. 6 2001 160
23. G. S. Attard, W. J. W. Morrow, P. Rajananthanan, US Patent 6673357 (2004).
24. For recent examples of glycosylation reactions:
25. J. Seibel, L. Hillringhaus, and R. Moraru Carbohydr. Res. 340 2005 507
26. G. Zhang, Q. Liu, L. Shi, and J. Wang Tetrahedron 64 2008 339
27. H. Shimizu, Y. Yoshimura, H. Hinou, and S.-I. Nishimura Tetrahedron 64 2008 10091
28. H. Hinou, N. Saito, M. Ogawa, T. Maeda, and S.-I. Nishimura Int. J. Mol. Sci. 10 2009 5285
29. C. Zandanel, C. Mioskowski, R. Baati, and A. Wagner Tetrahedron 65 2009 9395
30. J. Krag, M. S. Christiansen, J. G. Petersen, H. H. Jensen, Carbohydr. Res. 345 (2010) 872.
31. F. Mathew, K.N. Jayaprakash, B. Fraser-Reid, J. Mathew, and J. Scicinski Tetrahedron Lett. 44 2003 9051
32. Y. Yoshimura, H. Shimizu, H. Hinou, and S.-I. Nishimura Tetrahedron Lett. 46 2005 4701
33. T. Bililign, B.R. Griffith, and J.S. Thorson Nat. Prod. Rep. 22 2005 742 and references therein
34. M. Lei, L. Gao, and J.-S. Yang Tetrahedron Lett. 50 2009 5135
35. T. Matsumoto, T. Hosoya, and K. Suzuki Tetrahedron Lett. 31 1990 4629
36. C. Jaramillo, and S. Knapp Synthesis 1994 1
37. S.F. Martin Pure Appl. Chem. 75 2003 63
38. D.Y.W. Lee, and M. He Curr. Top. Med. Chem. 5 14 2005 1333
39. M. Bejugam, and S.L. Flitsch Org. Lett. 6 2004 4001
40. T. Cohen-Anisfeld, and P.T. Lansbury J. Am. Chem. Soc. 115 1993 10531
41. L.M. Likhosherstov, O.S. Novikova, V.A. Dervitskaya, and N.K. Kochetkov Carbohydr. Res 146 1986 C1
42. A. Lubineau, J. Augé, and B. Drouillat Carbohydr. Res. 266 1995 211
43. R.I. Hollingsworth, and G.J. Wang Chem. Rev. 100 2000 4267
44. M.T. Barros, K.T. Petrova, and A.M. Ramos J. Org. Chem. 69 2004 7772
45. M. Andrade, M.T. Barros, and P. Rodrigues Eur. J. Org. Chem. 2007 3655
46. M.M. Andrade, and M.T. Barros Tetrahedron 60 2004 9235
47. L.D.S. Yadav, and C. Awasthi Carbohydr. Res. 345 2010 318
48. B.G. Winchester Tetrahedron: Asymmetry 20 2009 645
49. A.L. Rousseau, P. Matlaba, and C.J. Parkinson Tetrahedron Lett. 48 2007 4079
50. M. Pagnotta, C.L.F. Pooley, B. Gurland, and M. Choi J. Phys. Org. Chem. 6 1993 407
51. C. Limousin, A. Olesker, J. Clophax, A. Petit, A. Loupy, and G. Lukacs Carbohydr. Res. 312 1998 23
52. L.H.B. Baptistella, A.Z. Neto, H. Onaga, and E.A.M. Godoi Tetrahedron Lett. 34 1993 8407
53. V. Chakraborty, and M.J. Bordoloi Chem. Res. 1999 118
54. F. Santoyo-González, and F. Hernández-Mateo Top. Heterocycl. Chem. 7 2007 133
55. C.O. Kappe Chem. Soc. Rev. 2010 DOI: 10.1039/b901973c
56. R. Lucas, V. Neto, A. Hadj Bouazza, R. Zerrouki, R. Granet, P. Krausz, and Y. Champavier Tetrahedron Lett. 49 2008 1004
57. J.A.F. Joosten, N.T.H. Tholen, F.A.E. Maate, A.J. Brouwer, G.W. van Esse, D.T.S. Rijkers, R.M.J. Liskamp, and R.J. Pieters Eur. J. Org. Chem. 2005 3182
58. A. Richel, P. Laurent, B. Wathelet, J.-P. Wathelet, and M. Paquot Tetrahedron Lett. 51 2010 1356
59. A. Richel, P. Laurent, B. Wathelet, J.-P. Wathelet, M. Paquot, unpublished results.
60. T.S. Hansen, J.M. Woodley, and A. Riisager Carbohydr. Res. 344 2009 2568
61. C. Li, Z. Zhang, and Z.K. Zhao Tetrahedron Lett. 50 2009 5403
62. X. Qi, M. Watanabe, T.M. Aida, and R.L. Smith Green Chem. 10 2008 799
63. S. Bradoo, P. Rathi, R.K. Saxena, and R.J. Gupta Biochem. Biophys. Methods 51 2002 115
64. J.R. Carrillo-Munoz, D. Bouvet, E. Guibé-Jampel, A. Loupy, and A. Petit J. Org. Chem. 61 1996 7746
65. M. Gelo-Pujic, E. Guibé-Jampel, A. Loupy, and A. Trincone J. Chem. Soc., Perkin Trans. 1 1997 1001
66. M. Gelo-Pujic, E. Guibé-Jampel, A. Loupy, S.A. Galema, and D. Mathé J. Chem. Soc., Perkin Trans. 1 1996 2777
67. L.D. Schmidt, and P.J. Dauenhauer Nature 447 2007 914
68. C. Vanderghem, P. Boquel, C. Blecker, and M. Paquot Appl. Biochem. Biotechnol. 2009 10.1007/s12010-009-8724-7
69. L. Olsson, and B. Hahn-Hagerdahl Enzyme Microb. Technol. 18 1996 312
70. G.G. Allan, B.B. Krieger, and D.W. Work J. Appl. Polym. 25 1980 1839
71. A. Orozco, A.D. Rooney, and G. Walker Trans IChemE, Part B. 85 B5 2007 446
72. Z. Zhang, and Z.K. Zhao Carbohydr. Res. 344 2009 2069
73. H. Ooshima, K. Aso, and Y. Harano Biotechnol. Lett. 6 1984 289
74. S. Zhu, Y. Wu, Z. Yu, C. Wang, F. Yu, S. Jin, Y. Ding, R. Chi, J. Liao, and Y. Zhang Biosyst. Eng. 93 2006 279
75. S. Zhu, Y. Wu, Z. Yu, Q. Chen, G. Wu, F. Yu, C. Wang, and S. Jin Biosyst. Eng. 93 2006 437
76. S. Zhu, Y. Wu, Z. Yu, X. Zhang, H. Li, and M. Gao Biores. Technol. 97 2006 1964
77. N. Gospodinova, A. Grelard, M. Jeannin, G.C. Chitanu, A. Carpov, A. Thiéry, and T. Besson Green Chem. 4 2002 220
78. R. Gourson, R. Benhaddou, P. Granet, P. Krausz, L. Saulnier, and J.-F. Thibault C. R. Acad. Sci. Paris, Ser. IIc 2 1999 75
79. C. Satgé, R. Granet, B. Verneuil, P. Branland, and P. Krausz C. R. Chimie 7 2004 135
80. S. Possidonio, L.C. Fidale, and O.A. El Seoud J. Polym. Sci. Part A: Polym. Chem. 48 2009 134
81. G. Antova, P. Vasvasova, and M. Zlatanov Carbohydr. Polym. 57 2004 131
82. J. Cléophax, M. Liagre, A. Loupy, and A. Petit Org. Proc. Res. Dev. 4 2000 498
83. M. Nüchter, B. Ondruschka, and W. Lautenschlarger Synth. Commun. 31 2001 1277