Preparation of 1-fluoroglycosides from 1-arylthio and 1-arylselenoglycosides using 4-methyl(difluoroiodo)benzene

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 149-156

  Caddick, S ^a   Gazzard, L ^a   Motherwell, W B ^b   Wilkinson, J A ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

GLYCOSIDE; ORGANOFLUORINE DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; FLUORINATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029655356     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00889-G     Document Type: Article

References (37)

1. Card, P. J.J. Carbohydr. Chem. 1985, 4, 451;
2. Micheel, F.; Klemer, A. Adv. Carb. Chem. 1961, 16, 85.
3. Nicolaou, K. C.; Seitz, S. P. Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430.
4. Fluorinated Carbohydrates: Chemical and Biochemical Aspects ed. N. F. Taylor, ACS Symposium Series 374, 1988.
5. Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189 and references therein;
6. Rosenbrook Jr., W.; Riley, D. A.; Lartey, D. A.Tetrahedron Lett. 1985, 26, 3;
7. Posner, G. H.; Haines, S. R. Tetrahedron Lett. 1985, 26, 5.
8. Pakulski, Z.; Pierozynski, D.; Zamojski, A. Tetrahedron 1994, 50, 2975;
9. Blomberg, I.; Norberg, T. J. Carb. Chem. 1992, 11, 751
10. Edmunds, J. J.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1989, 881;
11. For a general overview see Motherwell, W. B. Aldrichimica Acta 1992, 25, 71.
12. Edmunds, J. J.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1989, 1343.
13. Motherwell, W. B.; Wilkinson, J. A. Synlett 1991, 19.
14. Stork, G.; Zhao, K. Tetrahedron Lett. 1989, 30, 297.
15. Caddick, S.; Motherwell, W. B.; Wilkinson, J. A. J. Chem. Soc. Chem. Commun. 1991, 674.
16. Hanessian, S.; Bacquet, C.; Lehong, N. Carbohydr. Res. 1980, 86, C3;
17. Zissis, E.; Glingham, A. L.; Richtmeyer, N. K. Carbohydr. Res. 1966, 2, 461;
18. Purves, C. B. J. Am. Chem. Soc. 1929, 51, 3619;
19. Keck, G. E.; Enholm, E. J.; Kachensky, D. F. Tetrahedron Lett. 1984, 25, 1867 and references therein.
20. Giese, B.; Ruckert, B., Groninger, K. S.; Muhn, R.; Lindner, H-J. Leibigs Ann. Chem. 1988, 997.
21. Spryoudis, S.; Varvoglis, A. J. Chem. Soc. Chem. Commun. 1979, 615.
22. Sabesan, S.; Neira, S. J. Org. Chem. 1991, 56, 5468.
23. Bonner, W. A.; Robinson, A. J. Am. Chem. Soc. 1950, 72, 354.
24. Naumann, D.; Ruther, G. J. Fluorine Chem. 1980, 15, 213.
25. Hall, L. D.; Manville, J. F. J. Chem. Soc. Chem. Commun. 1968, 37;
26. b. Block, K.; Pederson, C.; Acta Chem.Scanda B 1975, 682.
27. Sharp, V. E.; Stacey, M. J. Chem. Soc. 1951, 285;
28. Hall, L. D.; Manville, J. F. Can. J. Chem. 1967, 45, 1299.
29. Kunz, H.; Sager, W. Helv. Chim. Acta 1985, 68, 283.
30. Wessel, H. P.; Englert, G.; Stangier, P. Helv. Chim. Acta 1991, 74, 682;
31. H.; Nishizawa, M. Tetrahedron 1992, 48, 3021;
32. Fukase, K.; Yoshimura, T.; Kotani, S.; Kusumoto, S. Bull Chem. Soc. Jpn. 1994, 473;
33. Ziegler, T.; Eckhardt, E.; Pantkowski, G. J. Carb. Chem. 1994, 13, 81;
34. Watanabe, Y.; Nakamoto, C.; Ozaki, S.; Sato, M.; Koizumu, K. J. Carb. Chem. 1993, 12, 685;
35. Dobarro-Rodriguez, A.; Trumtel, M.; Wessel, H. P. J. Carb. Chem. 1992, 11, 255;
36. Hall, L. D.; Manville, J. F. Chem. & Ind. 1965, 991;
37. Mukaiyama, T.; Murai, Y.; Shoda, S. Chem Lett. 1981, 431