Synthetic efforts towards the synthesis of fluorinated C-glycosidic analogues of α-galactosylceramides

Comptes Rendus Chimie

Volumn 15, Issue 1, 2012, Pages 57-67

  Leclerc, Eric ^a   Pannecoucke, Xavier ^a  

^a CNRS   (France)

Author keywords

Fluorine; Glycomimetics; Radical addition; Reformatsky reaction; galactosylceramides

Indexed keywords

EID: 84855715142     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2011.06.005     Document Type: Short Survey

References (81)

1. J.P. Bégué, and D. Bonnet-Delpon Bioorganic and medicinal chemistry of fluorine 2008 John Wiley & Sons, Inc Hoboken
2. P. Kirsch Modern Fluoroorganic Chemistry 2004 Wiley-VCH Weinheim, Germany
3. S. Purser, P.R. Moore, S. Swallow, and V. Gouverneur Chem. Soc. Rev. 37 2008 320
4. H.J. Böhm, D. Banner, S. Bendels, M. Kansy, B. Kuhn, K. Müller, U. Obst-Sander, and M. Stahl ChemBioChem. 5 2004 637
5. D. O'Hagan Chem. Soc. Rev. 37 2008 308
6. J.C. Biffinger, H.W. Kim, and S.G. DiMagno ChemBioChem. 5 2004 622 and references cited therein
7. A. Bondi J. Phys. Chem. 68 1964 441
8. T.R. Burke Jr. , and K. Lee Acc. Chem. Res. 36 2003 426
9. T.R. Burke Jr. , M.S. Smyth, A. Otaka, M. Nomizu, P.P. Roller, G. Wolf, R. Case, and S.E. Shoelson Biochemistry 33 1994 6490
10. G.M. Blackburn, D.L. Jakeman, A.J. Ivory, and M.P. Williamson Bioorg. Med. Chem. Lett. 4 1994 2573
11. T. Nakano, M. Makino, Y. Morizawa, and Y. Matsumura Angew. Chem. Int. Ed. Eng. 35 1996 1019 and references cited therein
12. X.L. Qiu, X.H. Xu, and F.L. Qing Tetrahedron 66 2010 789
13. R. Plantier-Royon, and C. Portella Carbohydrate Res. 327 2000 119
14. K. Dax, M. Albert, J. Ortner, and B.J. Paul Carbohydrate Res. 327 2000 47
15. K.W. Pankiewicz Carbohydrate Res. 327 2000 87
16. Y. Cheng, A.L. Guo, and D.S. Guo Curr. Org. Chem. 14 2010 977
17. T. Nishikawa, M. Adachi, and M. Isobe 2nd ed. B. Fraser Reid, K. Tatstuta, J. Thiem, G.L. Coté, S. Flitsch, Y. Ito, H. Kondo, S. Nishimura, B. Yu, Glycoscience: chemistry and chemical biology 3 2008 Springer Berlin Heidelberg 755 p
18. B. Vauzeilles, D. Urban, G. Doisneau, and J.M. Beau 2nd ed. B. Fraser Reid, K. Tatstuta, J. Thiem, G.L. Coté, S. Flitsch, Y. Ito, H. Kondo, S. Nishimura, B. Yu, Glycoscience: chemistry and chemical biology 3 2008 Springer Berlin Heidelberg 2021 p., and references cited therein
19. J.S. Houlton, W.B. Motherwell, B.C. Ross, M.J. Tozer, D.J. Williams, and A.M.Z. Slawin Tetrahedron 49 1993 8087
20. T. Brigaud, O. Lefebvre, R. Plantier-Royon, and C. Portella Tetrahedron Lett. 37 1996 6115
21. T.F. Herpin, W.B. Motherwell, and J.M. Weibel Chem. Commun. 1997 923
22. H. Berber, T. Brigaud, O. Lefebvre, R. Plantier-Royon, and C. Portella Chem. Eur. J. 7 2001 903
23. A. Wegert, R. Miethchen, M. Hein, and H. Reinke Synthesis 2005 1850
24. A. Wegert, M. Hein, H. Reinke, N. Hoffmann, and R. Miethchen Carbohydr. Res. 341 2006 2641
25. J. Picard, N. Lubin-Germain, J. Uziel, and J. Augé Synthesis 2006 979
26. G. Hirai, T. Watanabe, K. Yamaguchi, T. Miyagi, and M. Sodeoka J. Am. Chem. Soc. 129 2007 15420
27. K.A. Tony, R.W. Denton, A. Dilhas, J. Jiménez-Barbero, and D.R. Mootoo Org. Lett. 9 2007 1441
28. R.W. Denton, K.A. Tony, J.J. Hernandez-Gay, F.J. Canada, J. Jiménez-Barbero, and D.R. Mootoo Carbohydrate Res. 342 2007 1624
29. M. Kolympadi, M. Fontanella, C. Venturi, S. André, H.J. Gabius, J. Jimenez-Barbero, and P. Vogel Chem. Eur. J. 15 2009 2861
30. J.L. Chaytor, and R.N. Ben Biorg. Med. Chem. Lett. 20 2010 5251
31. B. Bernet, and A. Vasella Helv. Chim. Acta 62 1979 1990
32. A. Liptak, I. Jodal, and P. Nanasi Carbohydr. Res. 44 1975 1
33. S. Marcotte, F. D'Hooge, S. Ramadas, X. Pannecoucke, C. Féasson, and J.C. Quirion Tetrahedron Lett. 42 2001 5879
34. J.P. Pougny, M.A.M. Nassr, and P. Sinay J. Chem. Soc., Chem. Commun. 379 1981
35. J.W. Dankwardt, S.M. Dankwardt, and R.H. Schlessinger Tetrahedron Lett. 39 1998 4979
36. B. Rajanikanth, and R. Seshadri Tetrahedron Lett. 30 1989 755
37. R. Csuk, U. Franke, Z. Hu, and C. Krieger Tetrahedron 59 2003 7887
38. F. Orsini, and E. di Teodoro Tetrahedron: asymmetry 14 2003 2521
39. S. Hanessian, and C. Girard Synlett 1994 865
40. V. Grabberger, A. Berger, K. Dax, M. Fechter, G. Gradnig, and A. Stütz Liebigs Ann. Chem. 1993 379
41. R. Csuk, and B.I. Glänzer J. Carbohydr. Chem. 9 1990 797
42. V.K. Srivastava, and L.M. Lerner J. Org. Chem. 44 1979 3368 and references cited therein
43. A.B. Cuenca, F. D'Hooge, V. Gouge, G. Castelot-Deliencourt, H. Oulyadi, E. Leclerc, P. Jubault, X. Pannecoucke, and J.C. Quirion Synlett 2005 2627
44. S.A. Babirad, Y. Wang, and Y. Kishi J. Org. Chem. 52 1987 1370
45. G.A. Kraus, M.T. Molina, and J.A. Walling J. Chem. Soc., Chem. Commun. 1986 1568
46. D.H.R. Barton, S.I. Parekh, and C.L. Tse Tetrahedron Lett. 34 1993 2733
47. S.C. Dolan, and J. MacMillan J. Chem. Soc., Chem. Commun. 1985 1588
48. Géraldine Deliencourt-Godefroy, TF Chem company, unpublished results.
49. V. Gouge-Ibert, C. Pierry, F. Poulain, A.L. Serre, C. Largeau, V. Escriou, D. Scherman, P. Jubault, J.C. Quirion, and E. Leclerc Bioorg. Med. Chem. Lett. 20 2010 1957
50. G. Castelot Deliencourt-Godefroy, J.C. Quirion, EP 2009/2027138A2.
51. J.C. Quirion, X. Pannecoucke, F. D'Hooge, S. Marcotte, G. Castelot-Deliencourt, P. Jubault, V. Gouge, WO 2004/014928A2.
52. K. Sato, A. Tarui, T. Kita, Y. Ishida, H. Tamura, M. Omote, A. Ando, and I. Kumakadi Tetrahedron Lett. 45 2004 5735 5737
53. K. Kanai, and H. Wakabayashi T. Honda, Org. Lett. 2 2000 2549 2551
54. P. Allevi, M. Anastasia, P. Ciuffreda, A. Fiecchi, and A. Scala J. Chem. Soc., Chem. Commun. 1987 101
55. Y. Iseki, D. Kuroki, M. Asada, S. Takahashi, Y. Kishimoto, and Kobayashi Tetrahedron 30 1997 10271
56. F. Poulain, A.L. Serre, J. Lalot, E. Leclerc, and J.C. Quirion J. Org. Chem. 73 2008 2435
57. R. Mello, M. Fiorentino, O. Sciacovelli, and R. Curci J. Org. Chem. 53 1988 3890
58. W. Adam, R. Curci, and J.O. Edwards Acc. Chem. Res. 22 1989 205
59. D. Yang, M.K. Wong, and Y.C. Yip J. Org. Chem. 60 1995 3887
60. F. Poulain, E. Leclerc, and J.C. Quirion Tetrahedron Lett. 50 2009 1803
61. I. Dyong, J. Weigand, and H. Merten Tetrahedron Lett. 22 1981 2965
62. K. Takeda, E. Kaji, Y. Konda, N. Sato, H. Nakamura, N. Miya, A. Morizane, Y. Yanagisawa, A. Akiyama, S. Zen, and Y. Harigaya Tetrahedron Lett. 33 1992 7145
63. T.J. Donohoe, K. Blades, and M. Helliwell Chem. Commun. 1999 1733
64. W.R. Dolbier Jr Chem. Rev. 96 1996 1557
65. J. Hu, W. Zhang, and F. Wang Chem. Commun. 2009 7465 7478
66. R. Miethchen, M. Hein, and H. Reinke Eur. J. Org. Chem. 1998 919
67. T. Linker, T. Sommermann, and F. Kahlenberg J. Am. Chem. Soc. 119 1997 9377
68. D. Morel, and F. Dawans Tetrahedron 33 1977 1445
69. K. Sato, M. Omote, A. Ando, and I. Kumadaki J. Fluorine Chem. 125 2004 509
70. E. Godineau, C. Schäfer, and Y. Landais Org. Lett. 8 2006 4871
71. X. Yang, W. Yuan, S. Gu, X. Yang, F. Xiao, Q. Shen, and F. Wu J. Fluorine Chem. 128 2007 540
72. E. Godineau, K. Schenk, and Y. Landais J. Org. Chem. 73 2008 6983
73. M.G. Roepel Tetrahedron Lett. 43 2002 1973
74. B. Moreno, C. Quehen, M. Rose-Hélne, E. Leclerc, and J.C. Quirion Org. Lett. 9 2007 2477
75. L. Jean-Baptiste, S. Yemets, R. Legay, and T. Lequeux J. Org. Chem. 71 2006 2352
76. B. Quiclet-Sire, and S.Z. Zard Chem. Eur. J. 12 2006 6002
77. F.W. Lichtenthaler, M. Lergenmüller, S. Peters, and Z. Varga Tetrahedron: asymmetry 14 2003 727
78. F.W. Lichtenthaler, M. Lergenmüller, and S. Schwidetzky Eur. J. Org. Chem. 2003 3094
79. C.F. de Graauw, J.A. Peters, H. van Bekkum, and J. Huskens Synthesis 1994 1007
80. S. Colombel, M. Sanselme, E. Leclerc, J.C. Quirion, and X. Pannecoucke Chem. Eur. J. 17 2011 5238
81. D.J. Chambers, G.R. Evans, and A.J. Fairbanks Tetrahedron 60 2004 8411