Preparation of disaccharide haptens corresponding to Salmonella serogroups B and D

Journal of Carbohydrate Chemistry

Volumn 15, Issue 6, 1996, Pages 665-689

  Zegelaar Jaarsveld, Korien ^a   Van Der Plas, Simon C ^a   Van Der Marel, Gijs A ^a   Van Boom, Jacques H ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

SALMONELLA;

EID: 0003881583     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309608005684     Document Type: Article

References (34)

1. A.A. Lindberg, R. Wollins, G. Bruse, E. Ekwall, and S.B. Svenson, Am. Chem. Soc., Symp. Ser. 231, 83 (1983).
2. K. Jann, and O. Westphal, in The Antigens Volume 5, Ed., M. Sela, Academic Press, New York, 1975, 1.
3. a) C.G. Hellerqvist, B. Lindberg, S. Svensson, T. Holme, and A.A. Lindberg, Carbohydr. Res., 8, 43 (1968).
4. b) C.G. Hellerqvist, B. Lindberg, S. Svensson, T. Holme, and A.A. Lindberg, Carbohydr. Res., 9, 237 (1969).
5. C.G. Hellerqvist, O. Larm, B. Lindberg, T. Holme, and A.A. Lindberg, Acta Chem. Scand., 23, 1588 (1969).
6. a) N.K. Kochetkov, B.A. Dmitriev, A.Ya. Chernyak, and A.B. Levinsky, Carbohydr. Res., 110, C16 (1982).
7. b) A. Ya. Cherniak, A.B. Levinsky, and N.K. Kochetkov, Carbohydr. Res., 128, 269 (1984).
8. A. Ya. Cherniak, A.B. Levinsky, and N.K. Kochetkov, Bioorg. Khim., 14, 1047 (1988).
9. V. Horejsi, P. Smolek, and J. Kocourek, Biochem. Biophys. Acta, 538, 293 (1978).
10. G. Ekborg, P.J. Garegg, and B. Gotthamer, Acta Chem. Scand., B29, 765 (1975).
11. H. Borén, P.J. Garegg, and N.-H. Wallin, Acta Chem. Scand., 26, 1082 (1972).
12. K. Eklind, P.J. Garegg, and B. Gotthamer, Acta Chem. Scand., B29, 633 (1975).
13. a) G. Siewert, and O. Westphal, Liebigs Ann. Chem., 720, 171 (1968).
14. b) H.H. Baer, and D.J. Astles, Carbohydr. Res., 126, 343 (1984).
15. D.A. Prins, J. Am. Chem. Soc., 70, 3955 (1948).
16. S. Hanessian, and N.R. Plessas, J. Org. Chem., 34, 1035 (1969).
17. a) P.A.M. van der Klein. G.J.P.H. Boons, G.H. Veeneman, G.A. van der Marel, and J.H.van Boom, Tetrahedron Lett., 30, 5477 (1989).
18. b) P.A.M. van der Klein, G.J.P.H. Boons, G.H. Veeneman, G.A. van der Marel, and J.H. van Boom, Synlett, 311 (1990).
19. J.J.A. Beliën, G.A. van der Marel, and J.H. van Boom, to be published.
20. J.S. Brimacombe, and O.A. Ching, J. Chem. Soc., C, 1642 (1968).
21. B.M. Kim, and K.B. Sharpless, Tetrahedron Lett., 30, 655 (1989).
22. K. Sato, T. Hoshi, and Y. Kajihara, Chem. Lett., 1469 (1992).
23. a) S. Hanessian, and Y. Guindon, Tetrahedron Lett., 21, 2305 (1980).
24. b) S. Hanessian, and Y. Guindon, Carbohydr. Res., 86, C3 (1980).
25. M.J. Eis, and B. Ganem, Carbohydr. Res., 176, 316 (1988).
26. Y.-H. Chen, T.-Y. Luh, G.-H. Lee, and S.-M. Peng, J. Chem. Soc., Chem. Commun., 2369 (1994).
27. Y. Oikawa, T. Yoshioka, and O. Yonemitsu, Tetrahedron Lett., 23, 885 (1982).
28. The NMR spectroscopic data of 23 were in good accordance with those of its enantiomer. D.R. Bundle, and S. Josephson, Can. J. Chem., 59, 2686 (1978).
29. a) M. Haga, M. Chonan, and S. Tejima, Carbohydr. Res. 16, 486 (1971).
30. b) T. Iversen, and D.R. Bundle, Carbohydr. Res., 103, 29 (1982).
31. Upon completion of this paper, Bundle et al. described a similar reaction pathway to convert the anomeric methyl group into the corresponding thioethyl function. T.L. Lowary, E. Eichler, and D.R. Bundle, J. Org. Chem., 60, 7316 (1995).
32. J.F. King, and A.D. Albutt, Can. J. Chem., 48, 1754 (1970).
33. G.H. Veeneman, S.H. van Leeuwen, and J.H. van Boom, Tetrahedron Lett., 31, 1331 (1990).
34. G.H. Veeneman, S.H. van Leeuwen, H.M. Zuurmond, and J.H. van Boom, J. Carbohydr. Chem., 9, 783 (1990).