Synthesis of fluorine-containing core-2 tetrasaccharides

Synlett

Volumn , Issue 9 SPEC. ISS., 2003, Pages 1291-1294

  Xia, Jie ^a   Alderfer, James L ^a   Piskorz, Conrad F ^a   Locke, Robert D ^a   Matta, Khushi L ^a  

^a ROSWELL PARK CANCER INSTITUTE   (United States)

Author keywords

Core 2 O linked glycoproteins; Galactose residues; Tetrasaccharides

Indexed keywords

BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; DISACCHARIDE; FLUORINE; GALACTOSE; IMIDE;

ACETYLATION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; FLUORINATION; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; TEMPERATURE DEPENDENCE;

EID: 0037765605     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40342     Document Type: Article

References (31)

1. (a) Capon, C.; Laboisse, C. L.; Wieruszrski, J.-M.; Maoret, J. J.; Auheron, C.; Fournet, B. J. Biol. Chem. 1992, 267, 19248.
2. (b) Capon, C.; Wieruszeski, J.-M.; Lemoine, J.; Byrd, J. C.; Leffler, H.; Kim, Y. S. J. Biol. Chem. 1997, 272, 31957.
3. (c) Brockhausen, I. Biochem. Biophys. Acta 1999, 1473, 67.
4. (d) Rosen, S. D.; Bertozzi, C. R. Curr. Opin. Cell Biol. 1994, 6, 663.
5. (e) Brocke, C.; Kunz, H. Bioorg. Med. Chem. 2002, 10, 3085.
6. (a) Dwek, R. A. Chem. Rev. 1996, 96, 683.
7. (b) Lee, Y. C.; Lee, T. R. Acc. Chem. Res. 1995, 28, 321.
8. (c) Varki, A. Glycobiology 1993, 3, 97.
9. (a) Nicolaou, K. C.; Mitchell, H. J. Angew. Chem. Int. Ed. 2001, 40, 1576.
10. (b) Sanders, W. J.; Manning, D. D.; Koeller, K. M.; Kiessling, L. L. Tetrahedron 1997, 53, 16391.
11. (c) Wong, C.-H. Acc. Chem. Res. 1999, 32, 376.
12. (d) Gege, C.; Vogel, J.; Bendas, G.; Rothe, U.; Schmidt, R. R. Chem.-Eur. J. 2000, 6, 111.
13. (e) Herzner, H.; Reipen, T.; Schultz, M.; Kunz, H. Chem. Rev. 2000, 100, 4495.
14. (f) Lergenmuler, M.; Ito, Y.; Ogawa, T. Tetrahedron 1998, 54, 1381.
15. (g) Kanie, O.; Barresi, A.; Ding, Y.; Otter, Y.; Forsberg, L. S.; Ernst, B.; Hindsgaul, O. Angew. Chem., Int. Ed. Engl. 1995, 34, 2720.
16. (h) Jain, R. K.; Huang, B.-G.; Chandrasekaran, E. V.; Matta, K. L. Chem. Commun. 1997, 23.
17. (i) Huang, B.-G.; Jain, R. K.; Locke, R. D.; Alderfer, J. L.; Tabaczynski, W. A.; Matta, K. L. Tetrahedron Lett. 2000, 41, 6279.
18. (j) Xia, J.; Alderfer, J. L.; Piskorz, C. F.; Matta, K. L. Chem.-Eur. J. 2000, 6, 3442.
19. (k) Xia, J.; Alderfer, J. L.; Piskorz, C. F.; Matta, K. L. Chem.-Eur. J. 2001, 7, 356.
20. (a) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645.
21. (b) Howard, J. A. K.; Hoy, V. J.; O'Hagan, D.; Smith, G. T. Tetrahedron 1996, 53, 12613.
22. (a) Sarkar, A. K.; Rostand, K. S.; Jain, R. K.; Matta, K. L.; Esko, J. D. J. Biol. Chem. 1997, 272, 25608.
23. (b) Woynarowska, B.; Skrincosky, D. M.; Haag, A.; Sharma, M.; Matta, K. L.; Bernacki, R. J. J. Biol. Chem. 1994, 269, 22797.
24. (c) Sarkar, A. K.; Fritz, T. A.; Taylor, W. H.; Esko, J. D. Proc. Natl. Acad. Sci. USA 1995, 92, 3323.
25. (d) Goon, S.; Bertozzi, C. R. J. Carbohydr. Chem. 2002, 21, 943.
26. Card, P. J.; Reddy, C. S. J. Org. Chem. 1983, 48, 4734.
27. Kovac, P.; Yeh, H. J.; Glaudemans, C. P. Carbohydr. Res. 1985, 140, 277.
28. Jain, R. K.; Piskorz, C. F.; Chandrasekaran, E. V.; Matta, K. L. Carbohydr. Res. 1995, 271, 247.
29. (a) Koch, K.; Chambers, R. J. Carbohydr. Res. 1993, 241, 295.
30. (b) Dax, K.; Albert, M.; Ortner, J.; Paul, B. J. Carbohydr. Res. 2000, 327, 47.
31. -.