An efficient synthesis of CMP-3-fluoroneuraminic acid

Chemical Communications

Volumn , Issue 16, 1999, Pages 1525-1526

  Burkart, Michael D ^a   Vincent, Stéphane P ^a   Wong, Chi Huey ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NEURAMINIC ACID DERIVATIVE; SIALIC ACID; SIALYLTRANSFERASE;

ARTICLE; FLUORINATION; PHOSPHORYLATION; SYNTHESIS;

EID: 0033592105     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a903362i     Document Type: Article

References (27)

1. M. von Itztein and R. J. Thomson, Curr. Med. Chem., 1997, 4, 185.
2. S. Kelm and R. Schauer, Int. Rev. Cytol, 1997, 175, 137.
3. A. Harduin-Lepers, M. A. Recchi and P. Delannoy, Glycobiology, 1995, 5, 741.
4. T. Hayashi, B. Murray, R. Wang and C.-H. Wong, Bioorg. Med. Chem., 1997, 5, 497.
5. B. W. Murray, V. Wittmann, M. D. Burkart, S.-C. Hung and C.-H. Wong, Biochemistry, 1997, 36, 823.
6. B. Muller, C. Schaub and R. R. Schmidt, Angew. Chem., Int. Ed., 1998, 37, 2893.
7. B. Muller, T. J. Martin, C. Schaub and R. R. Schmidt, Tetrahedron Lett., 1998, 39, 509.
8. Y. Kajihara, H. Hashimoto, H. Kodama, T. Wakabayashi and K. Sato, J. Carbohydr. Chem., 1993, 12, 991.
9. Y. Kajihara, K. Kodama, T. Wakabayashi, K. Sato and H. Hashimoto, Carbohydr. Res., 1993, 247, 179.
10. B. A. Horenstein and M. Bruner, J. Am. Chem. Soc., 1996, 118, 10371.
11. T. Hagiwara, I. Kijima-Suda, T. Ido, H. Ohrui and K. Tomita, Carbohydr. Res., 1994, 263, 167.
12. C. R. Petrie, III., M. Sharma, O. D. Simmons and W. Korytnyk, Carbohydr. Res., 1989, 186, 326.
13. T. Nakajima, H. Hori, H. Ohrui, H. Meguro and T. Ido, Agric. Biol. Chem., 1988, 52, 1209.
14. M. D. Burkart, Z. Zhang, S.-C. Hung and C.-H. Wong, J. Am. Chem. Soc., 1997, 119, 11743 for synthesis of 3.
15. J. L.-C. Liu, G.-J. Shen, Y. Ichikawa, J. F. Rutan, G. Zapata, W. F. Vann and C.-H. Wong, J. Am. Chem. Soc., 1992, 114, 3901.
16. M. D. Chappell and R. L. Halcomb, J. Am. Chem. Soc., 1997, 119, 3393 for synthesis and application of 6.
17. A. Marra and P. Sinay, Carbohydr. Res., 1989, 190, 317.
18. K. C. Nicolaou, C. W. Hummel and Y. Iwabuchi, J. Am. Chem. Soc., 1992, 114, 3126.
19. V. Kumar, J. Kessler, M. E. Scott, B. H. Pathwarden, S. W. Tannenbaum and M. Flashner, Carbohydr. Res., 1981, 94, 123.
20. E. Schreiner, E. Zbiral, R. G. Kleineidam and R. Schauer, Liebigs Ann. Chem., 1991, 1991, 129.
21. V. Bolitt, C. Mioskowski, S.-G. Lee and J. R. Falck, J. Org. Chem., 1990, 55, 5812.
22. H. Ogura, K. Furuhata, H. Saito, G. Izumi, M. Itoh and Y. Shitori, Chem. Lett., 1984, 1003.
23. 3) -180.40 (dd).
24. U. Dabrowski, H. Friebolin, R. Brossmer and M. Supp, Tetrahedron, 1979, 48, 4637.
25. 23PCs, 1073; found 1073.
26. 16PNa, 655.1276; found 655.
27. J. Weinstein, U. deSousa-e-Silva and J. C. Paulson, J. Biol. Chem., 1982, 257, 13825.