The first synthesis of secondary sugar sulfonic acids by nucleophilic displacement reactions

Tetrahedron Letters

Volumn 45, Issue 4, 2004, Pages 839-842

  Lipták, András ^a   Balla, Edit ^a   Jánossy, Lóránt ^b   Sajtos, Ferenc ^a   Szilágyi, László ^b  

^a INSTITUTE OF EXPERIMENTAL MEDICINE   (Hungary)

^b UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA METHYLGLUCOSIDE; GLUCOSE DERIVATIVE; GLYCOSAMINOGLYCAN; LIGAND; OLIGOSACCHARIDE; SUGAR; SULFATE; SULFONIC ACID DERIVATIVE;

ARTICLE; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 0347418215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.025     Document Type: Article

References (25)

1. (a) Benson A.A., Daniel H., Wiser R. Proc. Natl. Acad. Sci. 45:1959;1582-1584
2. (b) Benson A.A. Adv. Lipid Res. 1:1963;387-394.
3. Miyano M., Benson A.A. J. Am. Chem. Soc. 84:1962;59-62.
4. Gigg R., Penglis A.A., Conant R. J. Chem. Soc., Perkin Trans. 1. 1980;2490-2493.
5. Gustafson K.R., Cardellina J.H., Fuller R.W., Weislow O.S., Kiser R.F., Snader K.M., Patterson G.M.L., Boyd M.R. J. Natl. Cancer Inst. 81:1989;1254-1258.
6. Gordon D.M., Danishefsky S.J. J. Am. Chem. Soc. 114:1992;659-663.
7. Reistad R. Carbohydr. Res. 54:1977;308-310.
8. (a) Hanashima S., Mizushina Y., Yamazaki T., Ohta K., Takahashi S., Koshino H., Sahara H., Sakaguchi K., Sugawara F. Tetrahedron Lett. 41:2000;4403-4407
9. (b) Hanashima S., Mizushina Y., Yamazaki T., Ohta K., Takahashi S., Sahara H., Sakaguchi K., Sugawara F. Bioorg. Med. Chem. 9:2001;367-376.
10. Sahara H., Ishikawa M., Takahashi N., Ohtani S., Sato N., Gasa S., Akino T., Kikuchi K. British J. Cancer. 75:1997;324-332.
11. Golik J., Dickey J.K., Todderud G., Lee D., Alford J., Huang S., Klohr S., Eustice D., Aruffo A., Agler M.L. J. Natl. Prod. 60:1997;387-389.
12. Loya S., Reshef V., Mizrachi E., Silberstein C., Rachamin Y., Carmeli S., Hizi A. J. Natl. Prod. 61:1998;891-895.
13. Musicki B., Widlanski T.S. Tetrahedron Lett. 32:1991;1267-1270.
14. Lipták A., Sajtos F., Jánossy L., Gehle D., Szilágyi L. Org. Lett. 5:2003;3671-3674.
15. Lipták A., Jodál I., Nánási P. Carbohydr. Res. 44:1975;1-11.
16. Ek M., Garegg P.J., Hultberg H., Oscarson S. J. Carbohydr. Chem. 2:1983;305-311.
17. Elhalabi J., Rice K.G. Carbohydr. Res. 335:2001;159-165.
18. Fernández-Bolaños J.G., Morales J., Garcia S., Diánez M.J., Dolores Estrada M., López-Castro A., Pérez S. Carbohydr. Res. 248:1993;1-14.
19. Hoch M., Heinz E., Schmidt R.R. Carbohydr. Res. 191:1989;21-28.
20. Reddie R.N. Synth. Commun. 17:1987;1129-1139.
21. Borbás A., Biró A., Lipták A. ACH-Models Chem. 131:1994;455-465.
22. (a) Winstein S., Allred E., Heck R., Glick R. Tetrahedron. 1958;1-13
23. (b) Brimacombe J.S., Ching O.A. J. Chem. Soc. C. 1968;1642-1646.
24. Mulard L.A., Kováç P., Glaudemans C.P.J. Carbohydr. Res. 259:1994;117-129.
25. 2,3=10.3 , H-3), 3.83 (dd, 1H, overlap, H-2), 3.22 (m, 2H, H-6a, 6b).