SN2 displacement of carbohydrate triflates by 9-oximes of erythromycin a and of a tylosin derivative

Journal of Carbohydrate Chemistry

Volumn 15, Issue 7, 1996, Pages 831-855

  Grandjean, Cyrille ^a   Lukacs, Gabor ^a  

^a INSTITUT DE CHIMIE DES SUBSTANCES NATURELLES   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030524577     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005695     Document Type: Article

References (41)

1. S. Omura in Macrolide Antibiotics. Chemistry, Biology and Practice, S. Omura, Ed.; Academic Press: New York, 1984.
2. a) G. Babany, D. Larrey and D. Pessayre, Prog. Drug Metab., 11, 61 (1988); b) T.M. Ludden, Clin. Pharmacokin., 10, 63 (1985).
3. a) G. Babany, D. Larrey and D. Pessayre, Prog. Drug Metab., 11, 61 (1988); b) T.M. Ludden, Clin. Pharmacokin., 10, 63 (1985).
4. H. Sakakibara and S. Omura in Macrolide Antibiotics. Chemistry, Biology and Practice, S. Omura Ed.; Academic Press: New York, 1984, p 85.
5. M. Delaforge, P. Ladam, G. Bouillé, J. Gharbi-Benarous, M. Jaouen and J.-P. Girault, Chem.-Biol. Interact., 85, 215 (1992).
6. a) M. Delaforge, M. Jaouen and D. Mansuy, Biochem. Pharmacol., 32, 2309 (1983); b) J. Gharbi-Benarous, P. Ladam, M. Delaforge and J.-P. Girault, J. Chem. Soc., Perkin Trans, I, 2303 (1993).
7. a) M. Delaforge, M. Jaouen and D. Mansuy, Biochem. Pharmacol., 32, 2309 (1983); b) J. Gharbi-Benarous, P. Ladam, M. Delaforge and J.-P. Girault, J. Chem. Soc., Perkin Trans, I, 2303 (1993).
8. G. Lukacs, C. Ruggeri-Duchatelle, A. Dessinges, A. Olesker, M. Laborde and L. Ming, Eur. Pat. Appl. 366 560, 1990.
9. J.-C. Gasc, S. Gouin d'Ambrières, A. Lutz and J.-F. Chantot, J. Antibiot. 44, 313 (1991).
10. P.A. Lartey and R. Faghih in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, G. Lukacs Ed.; Springer-Verlag: Berlin, 1993, p 121.
11. M. Pozo and V. Gotor, J. Chem. Soc., Perkin Trans. I, 1001 (1993).
12. a) J.M.J. Tronchet, D. Schazenbach, E. Winter-Mihaly, C. Diamantides, U. Likic, G. Galland-Barrera, C. Jurrand, K. Deen Pallie, J. Ohja-Poncet, J. Rupp and G. Moret, Helv. Chim. Acta, 65, 1404 (1982); b) E.M. Nashed, E. Grochowski and E. Czyzewska, Carbohydr. Res., 196, 184 (1990).
13. a) J.M.J. Tronchet, D. Schazenbach, E. Winter-Mihaly, C. Diamantides, U. Likic, G. Galland-Barrera, C. Jurrand, K. Deen Pallie, J. Ohja-Poncet, J. Rupp and G. Moret, Helv. Chim. Acta, 65, 1404 (1982); b) E.M. Nashed, E. Grochowski and E. Czyzewska, Carbohydr. Res., 196, 184 (1990).
14. a) J.M.J. Tronchet, G. Zosimo-Landolfo, G. Galland-Barrera and N. Dolahatshi, Carbohydr. Res., 204, 145 (1990); b) K.C. Nicolaou and R.C. Groneberg, J. Am. Chem. Soc., 112, 4085 (1990).
15. a) J.M.J. Tronchet, G. Zosimo-Landolfo, G. Galland-Barrera and N. Dolahatshi, Carbohydr. Res., 204, 145 (1990); b) K.C. Nicolaou and R.C. Groneberg, J. Am. Chem. Soc., 112, 4085 (1990).
16. 7 have reported the synthesis of (E)-9-O-erythromycin A oxime in 74% yield whereas the corresponding (E)9-O-methyloxime of erythromycin A was obtained in only 20% yield in the same conditions.
17. C. Grandjean, Thesis, University of Paris XI, 1994.
18. R.W. Binkley, M.G. Ambrose and D.G. Hehemann, J. Org. Chem., 45, 4387 (1980).
19. K. Dax, W. Wolflehner and H. Weidmann, Carbohydr. Res., 65, 132 (1978).
20. M.G. Ambrose and R.W. Binkley, J. Org. Chem., 48, 674 (1983).
21. L.A. Reed, III and L. Goodman, Carbohydr. Res., 94, 91 (1981).
22. R.W. Binkley, J. Org. Chem., 56, 3892 (1991).
23. T. Iwashige and H. Saeki, Chem. Phar. Bull., 15, 1803 (1967).
24. R. Johansson and B. Samuelsson, J. Chem. Soc., Perkin Trans. I, 2371 (1984).
25. S. Knapp, A.B.J. Naughton, C. Jaramillo and B. Pipik, J. Org. Chem., 57, 7328 (1992).
26. a) T. Iversen and D.R. Bundle, J. Chem. Soc., Chem. Commun., 1240 (1981); b) U. Widmer, Synthesis, 568 (1987).
27. a) T. Iversen and D.R. Bundle, J. Chem. Soc., Chem. Commun., 1240 (1981); b) U. Widmer, Synthesis, 568 (1987).
28. H.H. Baer and B. Radatus, Carbohydr. Res., 128, 165 (1984).
29. T. Ogawa and T. Kaburagi, Carbohydr. Res., 103, 53 (1982).
30. Y. Kondo, Carbohydr. Res., 30, 386 (1973).
31. H.B. Borén, P.J. Garegg, L. Kenne, L. Maron and S. Svensson, Acta Chem. Scand., 26, 644 (1972).
32. P.J. Garegg, T. Iversen and S. Oscarson, Carbohydr. Res., 50, C-12 (1976).
33. J.R. Turvey and T.P. Williams, J. Chem. Soc., 2119 (1962).
34. M. Ek, P.J. Garegg, H. Hultberg and S. Oscarson, J. Carbohydr. Chem., 2, 305 (1983).
35. A. Liptak, I. Jodal and P. Manasi, Carbohydr. Res., 44, 1 (1975).
36. F.H. Newth, S.D. Nicholas, F. Smith and L.F. Wiggins, J. Chem. Soc., 2550 (1949).
37. M.E. Evans, Carbohydr. Res., 21, 473 (1972).
38. During the preparation of this manuscript, synthesis of these triflates has been mentioned but their precise description not effected (a) or not given (b): a) M. Kassou and S. Castillon, J. Org. Chem., 60, 4353 (1995);
39. b) A. El Nemr and T. Tsuchiya, Tetrahedron Lett., 36, 7665 (1995).
40. Partial isomerisation of (E)9-erythromycin A oxime into the Z isomer in basic media has already been observed: see reference 7 and also R.R. Wilkening, R.W. Ratcliffe, G.A. Doss, K.F. Bartizal, A.C. Graham and C.M. Herbert, Bioorg. Med. Chem. Lett., 3, 1287 (1993).
41. A.C. Richardson, Carbohydr. Res., 10, 395 (1969).