Synthesis and GC-EIMS analyses of optically pure 3-hydroxy-2- azetidinones having N-sulfonamide drugs side chain

Synthetic Communications

Volumn 30, Issue 14, 2000, Pages 2465-2478

  Hassan, Hammed H A M ^a   Soliman, Raafat ^b  

^a Alexandria University Faculty Of Science   (Egypt)

^b Alexandria University Faculty of Pharmacy   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYACID; 3 HYDROXY 2 AZETIDINONE; ALKALOID; ALPHA AMINO ACID; BETA LACTAM ANTIBIOTIC; IMINE; IMINO ACID; KETENE DERIVATIVE; SULFONAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; STEREOMETRY; SYNTHESIS;

EID: 0034083745     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087410     Document Type: Article

References (31)

1. a) Southgate, R.; Branch, C.; Coulton, S. and Hunt, E. In "Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products"; Lukas, G., Ed., Springer-Verlag, Berlin 1993, vol.2, p.621,
2. b) Southgate, R. Contemp.Org. Synth., 1994, 1, 417,
3. c) Backes, J. In "Houben-Weyl, Methoden der Organischem Chemie", Muller, E., Bayer, O., Eds; Thieme: Stuttgart 1991, Band E16B, p.31.
4. Ojima, I. In "The Organic Chemistry of β-Lactams"; Georg, G. I., Ed; VCH publishers, New York 1992, pp. 197.
5. Morin, R. B. and Gorman, M., Eds. "Chemistry and Biology of β-Lactam Antibiotics", Academic Press, New York 1982-1983, vol. I-3.
6. a) Wasserman, H. H.; Leadbetter, M. R. and Kopka, I. E. Tetrahedron Lett., 1984, 25, 2391,
7. b) Wasserman, H. H.; Berger, G. D. and Cho, K. R. Tetrahedron Lett., 1982, 23, 465,
8. c) Bormann, D., Chem. Ber., 1970, 705, 1797.
9. Ojima, I.; Suga, S. and Abe, R. Chem. Lett., 1980, 853.
10. Ogliaruso, M. A. and Wolfe, J. F. In "Synthesis of Lactones and Lactams", updated from the Chemistry of Functional Groups, Patai, S. and Rappoport, Z., Eds, John Wiley&Sons; Chichester, New York 1993.
11. Staudinger, H. Liebigs Ann. Chem., 1907, 556, 51.
12. a) Cooper, R. D. G.; Daugherty, B. W. and Boyed, D. B. Pure Appl. Chem., 1987, 59, 485,
13. b) van der Steen, F. H. and van Koten, G. Tetrahedron, 1991, 47, 5703,
14. c) Georg, G. I. and Ravikumar, V.T. In "The Organic Chemistry of β-Lactams", Georg, G. I., Ed., VCH publishers; New York 1992, p. 295.
15. a) Imada, A.; Kitano, K.; Kintata, K.; Muroi, M. and Asai, M. Nature, 1981, 289, 590,
16. b) Stewart, W. W. Nature, 1971, 229, 174.
17. Fisher, J. D. and Knowles, J. R. Ann. Rep. Med. Chem., 1978, 13, 239.
18. Hattori, K.; Yoshida, T.; Nakashima, H.; Permanathan, M.; Aragaki, R.; Mimura, T.; Kaneko, Y.; Yamamoto, N. and Uryu, T. Carbohydr.Res., 1998, 312, 1.
19. Ram, V.J.; Srivastava, P.; Singh, S. K.; Kandpal, M. and Tekwani, B. L. Bioorg. Med. Chem. Lett., 1997, 7, 1087.
20. a) Hubschwerlen, C. and Schmid, G., Helv. Chim. Acta, 1983, 66, 2206,
21. b) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S. and Wagle, D. R. Tetrahedron, 1992, 48, 4831.
22. a) Hassan, H. H. A. M. unpublished results,
23. b) Pallavicini, M.; Valoti, E.; Villa, L. and Piccolo, O. Tetrahedron: Asymmetry, 1994, 5, 5.
24. a) Dondoni, A. and Merino, P. Org. Synth., 1993, 72, 21,
25. b) Baer, E. and Fischer, H. O. L J. Biol. Chem., 1939, 128, 463.
26. Manhas, M. S.; Amin, S. G.; Chawla, H. P. S. and Bose, A. K. J. Heterocydic Chem., 1978, 15, 601.
27. a) Kagan, H. B.; Basselier, J. J. and Lache, J. L. Tetrahedron Lett., 1964, 941,
28. b) Alcaide, B.; Polanco, C. and Sierra, M. A. Synlett, 1998, 416 and references cited therein.
29. a) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R. and Hegde, V. R. In Third International Symposium on "Recent Advances in the Chemistry of β-Lactam Antibiotics", Brown, A. G. and Roberts, S. M., Eds., spes. Publ. No. 52, The Royal Society of Chemistry, July 1984, p.387,
30. b) Bose, A. K.; Manhas, M. S.; van der Veen, J. M.; Bari, S. S.; Wagle, D. R.; Hegde, V. R. and Krishnan, L. Tetrahedron Lett., 1985, 26, 33.
31. Hassan, H. H. A. M. and Soliman, R. Abstracts of Papers, XVIIIth International Carbohydrate Symposium, Milan, Italy, July 21-26, 1996, PB 001, p. 259.