C-Difluoromethylene-containing, C-trifluoromethyl and C-perfluoroalkyl carbohydrates. Synthesis by carbohydrate transformation or building block methods

Carbohydrate Research

Volumn 327, Issue 1-2, 2000, Pages 119-146

  Plantier Royon, Richard ^a   Portella, Charles ^a  

^a CNRS   (France)

Author keywords

C Perfluoroalkyl carbohydrates; C Difluoromethylene carbohydrates; C Trifluoromethyl carbohydrates; Fluorinated synthons

Indexed keywords

C DIFLUOROMETHYLENE DERIVATIVE; C TRIFLUOROMETHYL DERIVATIVE; CARBOHYDRATE DERIVATIVE; UNCLASSIFIED DRUG;

CARBOHYDRATE SYNTHESIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; FLUORINATION; GLYCOSYLATION; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; REVIEW;

CARBOHYDRATES; FLUORINE; FLUOROCARBONS; MOLECULAR STRUCTURE;

EID: 0034631786     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(00)00034-3     Document Type: Review

References (102)

1. (a) P.J. Card, J. Carbohydr. Chem., 4 (1985) 451-487.
2. (b) N.F. Taylor (Ed.), Fluorinated Carbohydrates, Chemical and Biochemical Aspects, ACS Symp. Ser. 374, American Chemical Society, Washington, DC, 1988.
3. (c) I. Ojima, J.R. McCarthy, J.T. Welch, (Eds.), Biomedical Frontiers of Fluorine Chemistry, ACS Symp. Ser. 639, American Chemical Society, Washington, DC, 1996.
4. (a) J.G. Riess, J. Greiner, in: G. Descotes (Ed.), Carbohydrates as Organic Raw Materials II, VCH, Weinheim, 1992, pp. 209-259.
5. (b) J.G. Riess, M.-P. Krafft, Biomaterials, 19 (1998) 1529-1539.
6. (c) M.-P. Krafft, J.G. Riess, Biochimie, 80 (1998) 489-514.
7. (a) S.J. Williams, S.G. Withers, this issue.
8. (b) B. Beutieu-Baumann, K. Hamachi, F. Oberdozfez, J. Steinbach, this issue.
9. (a) J.G. Riess, J. Greiner, this issue.
10. (b) R. Miethchen, M. Hein, this issue.
11. Tozer M.J., Herpin T. Tetrahedron. 52:1996;8619-8683.
12. Naae D.G., Burton D.J. Synth. Commun. 3:1973;197-200.
13. (a) S.I. Hayashi, T. Nakai, N. Ishikawa, D.J. Burton, D.G. Naae, H.S. Kesling, Chem. Lett., (1979) 983-986.
14. (b) D.J. Burton, H.S. Kesling, D.G. Naae, J. Fluorine Chem., 18 (1981) 293.
15. Burton D.J., Yang Z.-Y., Qiu W. Chem. Rev. 96:1996;1641-1715.
16. Tronchet J.M.J., Bonenfant A.P. Helv. Chim. Acta. 63:1980;1644-1653.
17. Tronchet J.M.J., Bonenfant A.P., Barbalat-Rey F. Carbohydr. Res. 67:1978;564-573.
18. Tronchet J.M.J., Schwarzenbach D., Barbalat-Rey F. Carbohydr. Res. 46:1976;9-17.
19. Yamazaki T., Hiraoka S., Kitazume T. Tetrahedron: Asymm. 8:1997;1157-1160.
20. S. Hiraoka, T. Yamazaki, T. Kitazume, Synlett, (1997) 669-670.
21. Serafinowski P.J., Barnes C.L. Tetrahedron. 52:1996;7929-7938.
22. W.B. Motherwell, M.J. Tozer, B.C. Ross, J. Chem. Soc., Chem. Commun., (1989) 1437-1439.
23. Houlton J.S., Motherwell W.B., Ross B.C., Tozer M.J., Williams D.J., Slawin A.M.Z. Tetrahedron. 49:1993;8087-8106.
24. Sabol J.S., McCarthy J.R. Tetrahedron Lett. 33:1992;3101-3104.
25. W.B. Motherwell, B.C. Ross, M.J. Tozer, Synlett, (1989) 68-70.
26. Herpin T.F., Motherwell W.B., Tozer M.J. Tetrahedron: Asymm. 5:1994;2269-2282.
27. T.F. Herpin, W.B. Motherwell, J.-M. Weibel, Chem. Commun. (Cambridge), (1997) 923-924.
28. Brigaud T., Lefebvre O., Plantier-Royon R., Portella C. Tetrahedron Lett. 37:1996;6115-6116.
29. T. Brigaud, P. Doussot, C. Portella, J. Chem. Soc., Chem. Commun., (1994) 2117-2118.
30. H. Berber, T. Brigaud, O. Lefebvre, R. Plantier-Royon, C. Portella, in preparation.
31. (a) G.M. Blackburn, D. Brown, S.J. Martin, M.J. Parratt, J. Chem. Soc., Perkin Trans. 1, (1987) 181-186.
32. (b) G.M. Blackburn, D.E. Kent, J. Chem. Soc., Perkin Trans. 1, (1986) 913-917.
33. (c) G.M. Blackburn, D. Brown, S.J. Martin, J. Chem. Res., (1985) 92-93.
34. (d) G.M. Blackburn, T.D. Peree, A. Rashid, C. Bisbal, B. Lebleu, Chem. Scrip., 26 (1986) 21.
35. (e) G.M. Blackburn, F. Eckstein, D.E. Kent, T.D. Peree, Nucleosides Nucleotides, 4 (1985) 165-173.
36. (f) G.R.J. Thatcher, A.S. Campbell, J. Org. Chem., 58 (1993) 2271-2281.
37. (g) R.D. Chambers, R. Jaouhari, D. O'Hagan, Tetrahedron, 45 (1989) 5101-5108.
38. (h) S. Halazy, A. Ehrhard, C. Danzin, J. Am. Chem. Soc., 113 (1991) 315-317.
39. (a) M. Obayashi, I. Eiji, K. Matsui, K. Kondo, Tetrahedron Lett., 23 (1982) 2323-2326.
40. (b) M. Obayashi, K. Kondo, Tetrahedron Lett., 23 (1982) 2327-2328.
41. R.D. Chambers, R. Jahouari and D. O'Hagan, J. Chem. Soc., Chem. Commun., (1988) 1169-1170.
42. Vinod T.K., Griffith O.H., Keana J.F.W. Tetrahedron Lett. 35:1994;7193-7196.
43. Berkowitz D.B., Shen Q., Maeng J.-H. Tetrahedron Lett. 35:1994;6445-6448.
44. (a) D.B. Berkowitz, D.G. Sloss, J. Org. Chem., 60 (1995) 7047-7050.
45. (b) D.B. Berkowitz, D. Bhuniya, G. Peris, Tetrahedron Lett., 40 (1999) 1869-1872.
46. Matulic-Adamic J., Haeberli P., Usman N. J. Org. Chem. 60:1995;2563-2569.
47. Berkowitz D.B., Sloss D.G. J. Org. Chem. 60:1995;7047-7050.
48. Martin S.F., Dean D.W., Wagman A.S. Tetrahedron Lett. 33:1992;1839-1842.
49. S.G. Levy, D.B. Wasson, D.A. Carson, H.B. Cottam, Synthesis, (1996) 843-846.
50. J.-B. Behr, C. Mvondo Evina, N. Phung, G. Guillerm, J. Chem. Soc., Perkin Trans. 1, (1997) 1597-1599.
51. T.F. Herpin, J.S. Houlton, W.B. Motherwell, B.P. Roberts, J.-M. Weibel, Chem. Commun. (Cambridge), (1996) 613-614.
52. Herpin T.F., Motherwell W.B., Roberts B.P., Roland S., Weibel J.-M. Tetrahedron. 53:1997;15085-15100.
53. Kaneko S., Yamazaki T., Kitazume T. J. Org. Chem. 58:1993;2302-2312.
54. Kitazume T., Murata K., Okabe A., Takahashi Y., Yamazaki T. Tetrahedron: Asymm. 5:1994;1029-1040.
55. Kitazume T., Shibano H. J. Fluorine Chem. 82:1997;185-188.
56. A. Arnone, P. Bravo, M. Frigerio, F. Viani, C. Zappalà, Synthesis, (1998) 1511-1518.
57. Ruppert I., Schlich K., Volbach W. Tetrahedron Lett. 25:1984;2195-2198.
58. Prakash G.K.S., Yudin A.K. Chem. Rev. 97:1997;757-786.
59. R.C. Bansal, B. Dean, S.-I. Hakomori, T. Toyokuni, J. Chem. Soc,. Chem. Commun., (1991) 796-798.
60. Munier P., Giudicelli M.-B., Picq D., Anker D. J. Carbohydr. Chem. 13:1994;1225-1230.
61. Munier P., Picq D., Anker D. Tetrahedron Lett. 34:1993;8241-8244.
62. Munier P., Giudicelli M.-B., Picq D., Anker D. J. Carbohydr. Chem. 15:1996;739-762.
63. Munier P., Krusinski A., Picq D., Anker D. Tetrahedron. 51:1995;1229-1244.
64. A.P. Kozikowski, V.I. Ognyanov, A.H. Fauq, R.A. Wilcox, S.R. Nahorski, J. Chem. Soc., Chem. Commun, (1994) 599-600.
65. C. Schmit, Synlett, (1994) 241-242.
66. Johnson C.R., Bhumralkar D.R., De Clercq E. Nucleosides Nucleotides. 14:1995;185-194.
67. Lavaire S., Plantier-Royon R., Portella C. J. Carbohydr. Chem. 15:1996;361-370.
68. Lavaire S., Plantier-Royon R., Portella C., de Monte M., Kirn A., Aubertin A.-M. Nucleosides Nucleotides. 17:1998;2267-2280.
69. Kozak J., Johnson C.R. Nucleosides Nucleotides. 17:1998;2221-2239.
70. Hanzawa Y., Uda J.-I., Kobayashi Y., Ishido Y., Taguchi T., Shiro M. Chem. Pharm. Bull. 9:1991;2459-2461.
71. Lavaire S., Plantier-Royon R., Portella C. Tetrahedron: Asymm. 9:1998;213-226.
72. Foulard G., Brigaud T., Portella C. J. Fluorine Chem. 91:1998;179-183.
73. Foulard G., Brigaud T., Portella C. J. Org. Chem. 62:1997;9107-9113.
74. J.-L. Clavel, B. Langlois, R. Nantermet, M. Tordeux, C. Wakselman, J. Chem. Soc., Perkin Trans. 1, (1992) 3371-3375.
75. R. Miethchen, M. Hein, H. Reinke, Eur. J. Org. Chem., (1998) 919-923.
76. Tellier F., Sauvêtre R. J. Fluorine Chem. 62:1993;183-189.
77. Hiraoka S., Yamazaki T., Kitazume T. Heterocycles. 47:1998;129-132.
78. S. Hiraoka, T. Yamazaki, T. Kitazume, Chem. Commun. (Cambridge), (1997) 1497-1498.
79. Kawada K., Kitagawa O., Taguchi T., Hanzawa Y., Kobayashi Y., Iitaka Y. Chem. Pharm. Bull. 33:1985;4216-4222.
80. (a) T. Yamazaki, K. Mizutani, M. Takeda, T. Kitazume, J. Chem. Soc., Chem. Commun., (1992) 55-57.
81. (b) T. Yamazaki, K. Mizutani, T. Kitazume, J. Synth. Org. Chem. Jpn., 52 (1994) 734-745.
82. (c) T. Yamazaki, K. Mizutani, T. Kitazume, Tetrahedron: Asymmetry, 4 (1993) 1059-1062.
83. (d) T. Yamazaki, K. Mizutani, T. Kitazume, J. Org. Chem., 58 (1993) 4346-4359.
84. (e) T. Yamazaki, K. Mizutani, T. Kitazume, in: I. Ojima, J.R. McCarthy, J.T. Welch (Eds.), Biomedical Frontiers of Fluorine Chemistry, ACS Symposium Series 639, 1996, pp. 105-116.
85. Itoh K., Takeda M., Namekawa M., Nayuki S., Murayama Y., Yamazaki T., Kitazume T. Ferroelectrics. 148:1993;85-102.
86. (a) K. Mizutani, T. Yamazaki, T. Kitazume, J. Chem. Soc., Chem. Commun., (1995) 51-52.
87. (b) T. Yamazaki, K. Mizutani, T. Kitazume, J. Org. Chem., 60 (1995) 6046-6056.
88. Y. Morisawa, A. Yasuda, K. Uchida, Jpn Kokai Tokyo Koho Jp 02270893, A2 (1989); Chem. Abstr., 114 (1991) 143939w.
89. Wucherpfennig U., Logothetis T.A., Eilitz U., Burger K. Tetrahedron. 52:1996;143-148.
90. Logothetis T.A., Eilitz U., Hiller W., Burger K. Tetrahedron. 54:1998;14023-14030.
91. Differding E., Frick W., Lang R.W., Martin P., Schmit C., Veenstra S., Greuter H. Bull. Soc. Chim. Belg. 99:1990;647-671.
92. Hayman C.M., Laesen D.S., Brooker S. Aust. J. Chem. 51:1998;545-553.
93. For a review on perfluoroorganometallic reagents, see: D.J. Burton, Z.-Y. Yang, Tetrahedron, 48 (1992) 189-275.
94. S. Lavaire, R. Plantier-Royon, C. Portella, Eur. Patent 819697 (1998), Fr. Demande FR 2,750,134 Chem. Abstr., 128 (1998) P 115193u.
95. D. Peters, C. Zur, R. Miethchen, Synthesis, (1998) 1033-1038.
96. Peters D., Zur C., Miethchen R. Liq. Cryst. 24:1998;695-699.
97. Dolbier W.R. Jr. Chem. Rev. 96:1996;1557-1584.
98. (a) W.-Y. Huang, Y. Xie, Chin. J. Chem., 9 (1991) 351-359.
99. (b) W.-Y. Huang, J. Fluorine Chem., 58 (1992) 1-8.
100. C. Zur, R. Miethchen, Eur. J. Org. Chem., (1998) 531-539.
101. Bergeron S., Brigaud T., Foulard G., Plantier-Royon R., Portella C. Tetrahedron Lett. 35:1994;1985-1988.
102. G. Foulard, Ph.D. Dissertation, University of Reims, January 1997.