Asymmetric synthesis of N-acetylneuraminic acid

Chemical Communications

Volumn , Issue 3, 2000, Pages 227-228

  Kang, Sung Ho ^a   Choi, Hyeong Wook ^a   Kim, Joon Seop ^a   Youn, Joo Hack ^b  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

^b SunMoon University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

N ACETYLNEURAMINIC ACID;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; ENANTIOMER; STEREOCHEMISTRY; SYNTHESIS;

EID: 0003089743     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a909400h     Document Type: Article

References (30)

1. Sialic Acids: Chemistry, Metabolism and Function in Cell Biology Monographs, ed. R. Schauer, Springer Verlag, Wien, New York, 1982, vol. 10.
2. M. von Itzstein and R. J. Thompson, Top. Curr. Chem., 1997, 186, 119.
3. R. B. Kemp, J. Cell Sci., 1970, 6, 751.
4. R. Schauer, Pure Appl. Chem., 1984, 56, 797; R. Schauer, Trends Biochem. Sci., 1985, 10, 357.
5. R. Schauer, Pure Appl. Chem., 1984, 56, 797; R. Schauer, Trends Biochem. Sci., 1985, 10, 357.
6. J. M. Jancik, R. Schauer and H. J. Z. Streicher, Physiol. Chem., 1975, 356, 1329.
7. F. Ahmad and P. McPhie, Int. J. Biochem., 1980, 11, 91.
8. E. Zbiral, E. Schreiner, R. Chiristian, R. G. Kleineidam and R. Schauer, Liebigs Ann. Chem., 1989, 159.
9. M. Hartann, R. Chiristian and E. Zbiral, Liebigs Ann. Chem., 1990, 83; E. Schreiner, R. Chiristian and E. Zbiral, Liebigs Ann. Chem., 1990, 93.
10. M. Hartann, R. Chiristian and E. Zbiral, Liebigs Ann. Chem., 1990, 83; E. Schreiner, R. Chiristian and E. Zbiral, Liebigs Ann. Chem., 1990, 93.
11. A. Gottschalk, Nature, 1951, 167, 845; M. Czarnicki and E. Thornton, J. Am. Chem. Soc., 1977, 99, 8279.
12. A. Gottschalk, Nature, 1951, 167, 845; M. Czarnicki and E. Thornton, J. Am. Chem. Soc., 1977, 99, 8279.
13. W. Spevak, J. O. Nagy, D. H. Charych, M. E. Schaefer, J. H. Gilbert and M. D. Bednarski, J. Am. Chem. Soc., 1993, 115, 1146; A. Giannis, Angew. Chem., Int. Ed. Engl., 1994, 33, 178.
14. W. Spevak, J. O. Nagy, D. H. Charych, M. E. Schaefer, J. H. Gilbert and M. D. Bednarski, J. Am. Chem. Soc., 1993, 115, 1146; A. Giannis, Angew. Chem., Int. Ed. Engl., 1994, 33, 178.
15. For the references of earlier syntheses, see (a) M. P. DeNinno, Synthesis, 1991, 583;
16. (b) T. Yamamoto, T. Teshima, K. Inami and T. Shiba, Tetrahedron Lett., 1992, 32, 325;
17. (c) L.-H. Lin, T. Sugai, R. L. Halcomb, Y. Ichigawa and C.-H. Wong, J. Am. Chem. Soc., 1992, 114, 10 138;
18. (d) D. M. Gordon and G. M. Whitesides, J. Org. Chem., 1993, 58, 7937;
19. (e) T.-H. Chan and M.-C. Lee, J. Org. Chem., 1995, 60, 4228;
20. (f) T. Takahashi, H. Tsukamoto, M. Kurosaki and H. Yamada, Synlett, 1997, 1065.
21. S. J. Danishefsky, M. P. DeNinno and S. Chen, J. Am. Chem. Soc., 1988, 110, 3929.
22. M. Banwell, C. D. Savi and K. Watson, J. Chem. Soc., Perkin Trans. 1, 1988, 2251.
23. S. H. Kang and J. S. Kim, Chem. Commun., 1998, 1353.
24. S. David and S. Hanessian, Tetrahedron, 1985, 41, 643.
25. H. H. Wasserman and W.-B. Ho, J. Org. Chem., 1994, 59, 4364.
26. (a) J. Haverkamp, H. Van Halbeek, L. Donald, J. F. G. Vliegenthart, R. Pfeil and R. Schauer, Eur. J. Biochem., 1982, 122, 305;
27. (b) F. Baumberger and A. Vasella, Helv. Chim. Acta, 1986, 69, 1205;
28. (c) A. Marra and P. Sinay, Carbohydr. Res., 1989, 190, 317.
29. The spectroscopic data of the synthetic 20 and 21 are identical to those of 20 and 21 prepared from the commercially available Neu5Ac 1 (Aldrich).
30. All new compounds showed satisfactory spectral data.