A regio- and stereo-selective introduction of azide at C-4 of 2,3-unsaturated N-acetylneuraminic acids

Carbohydrate Research

Volumn 302, Issue 3-4, 1997, Pages 237-240

  Kok, Gaik B ^a   Von Itzstein, Mark ^a  

^a MONASH UNIVERSITY   (Australia)

Author keywords

Glycal; N acetylneuramine acid; Sialikc acid; Thioisostere; Ulosonic acid

Indexed keywords

N ACETYLNEURAMINIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0030744477     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0008-6215(97)00124-9     Document Type: Article

References (12)

1. A.P. Corfield and R. Schauer, in R. Schauer (Ed.), Sialic Acids: Chemistry, Metabolism and Function; Cell Biology Monograph, Vol. 10, Springer, New York, 1982, pp. 5-39.
2. M. von Itzstein and R.J. Thomson, in J. Thiem and H. Driguez (Eds.), The Synthesis of Novel Sialic Acids as Biological Probes; Topics in Current Chemistry, Springer, Heidelberg, 1997, pp. 119-170.
3. M. von Itzstein, W.-Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T. Van Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.G. Hotham, J.M. Cameron, and C.R. Penn, Nature, 363 (1993) 418-423; M. von Itzstein, W.-Y. Wu, and B. Jin, Carbohydr. Res., 259 (1994) 301-305.
4. M. von Itzstein, W.-Y. Wu, G.B. Kok, M.S. Pegg, J.C. Dyason, B. Jin, T. Van Phan, M.L. Smythe, H.F. White, S.W. Oliver, P.M. Colman, J.N. Varghese, D.M. Ryan, J.M. Woods, R.C. Bethell, V.G. Hotham, J.M. Cameron, and C.R. Penn, Nature, 363 (1993) 418-423; M. von Itzstein, W.-Y. Wu, and B. Jin, Carbohydr. Res., 259 (1994) 301-305.
5. G.B. Kok, M. Campbell, B.L. Mackey, and M. von Itzstein, J. Chem. Soc., Perkin Trans. 1, (1996) 2811-2815.
6. V. Kumar, J. Kessler, M.E. Scott, B.H. Patwardham, S.W. Tanenbaum, and M. Flashner, Carbohydr. Res., 94 (1981) 123-130.
7. G.B. Kok, D.R. Groves, and M. von Itzstein, J. Chem. Soc., Chem. Commun., (1996) 2017-2018.
8. M. von Itzstein, B. Jin, W.-Y. Wu, and M. Chandler, Carbohydr. Res., 244 (1993) 181-185.
9. E. Schreiner, E. Zbiral, R.G. Kleineidam, and R. Schauer, Liebigs Ann. Chem., (1991) 129-134.
10. S.-I. Murahashi, Y. Taniguchi, Y. Imada, and Y. Tanigawa, J. Org. Chem., 54 (1989) 3292-3303.
11. N. Vicart, B. Cazes, and J. Goré, Tetrahedron Lett., 36 (1995) 535-538.
12. D.P. Curran and Y.G. Suh, Carbohydr. Res., 171 (1987) 161-191.