First direct glycosylation of unprotected nonreducing mono- and disaccharides

European Journal of Organic Chemistry

Volumn , Issue 33, 2007, Pages 5506-5513

  Steinmann, Andreas ^a   Thimm, Julian ^a   Thiem, Joachim ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Combinatorial chemistry; Glycosylation; Sacharides; Single step reactions

Indexed keywords

EID: 36349001729     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700504     Document Type: Article

References (32)

1. P. Arya, R. N. Ben, K. M. K. Kutterer, Combinatorial Chemistry for the Synthesis of Carbohydrates/Carbohydrate Mimics Libraries ("Organic Synthesis Highlights IV"), Wiley-VCH, 2000, p. 337-342.
2. B. Yu, B. Li, G. Xing, Y. Hui, J. Comb. Chem. 2001, 3, 404-406.
3. Y. Ding, J. Labbe, O. Kanie, O. Hindsgaul, Bioorg. Med. Chem. 1996, 4, 683-692.
4. O. Kanie, F. Barresi, Y. Ding, J. Labbe, A. Otter, L. S. Forsberg, B. Ernst, O. Hindsgaul, Angew. Chem. Int. Ed. Engl. 1995, 34, 2720-2722.
5. D. Kahne, Science 1996, 274, 1520-1522.
6. P. M. St. Hilaire, M. Meldal, Angew. Chem. Int. Ed. 2000, 39, 1163-1179.
7. P. Arya, R. N. Ben, Angew. Chem. Int. Ed. Engl. 1997, 36, 1280-1282.
8. G.-J. Boons, B. Heskamp, F. Hout, Angew. Chem. Int. Ed. Engl. 1996, 35, 2845-2847.
9. R. Liang, L. Yan, J. Loebach, M. Ge, Y. Uozumi, K. Sekanina, N. Horan, J. Glidersleeve, C. Thomson, A. Smith, K. Biswas, W. C. Still, D. Kahne, Science 1996, 274, 1520-1522.
10. O. J. Plante, Comb. Chem. High Throughput Screening 2005, 8, 153-159.
11. S. N. Baytas, R. J. Linhardt, Mini-Rev. Org. Chem. 2004, 1, 27-39.
12. O. Kanie, O. Hindsgaul in: Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries (Ed.: P. H. Seeberger), Wiley, New York 2001, p. 239-256;
13. G.-J. Boons, T. Zhu, in: Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries (Ed.: P. H. Seeberger), Wiley, New York 2001, p. 201-211;
14. E. E. Simanek, C.-H. Wong, in: Solid Support Oligosaccharide Synthesis and Combinatorial Carbohydrate Libraries (Ed.: P. H. Seeberger), Wiley, New York 2001, p. 213-238.
15. A. Michael, Compt. Rend. 1879, 89, 6.
16. E. Fischer, K. Raske, Ber. Dtsch. Chem. Ges. 1909, 42, 1465-1476.
17. R. M. Hann, J. Am. Chem. Soc. 1934, 56, 1631.
18. K. Krohn, J. Thiem, J. Chem. Soc. Perkin Trans. 1 1977, 10, 1186-1190.
19. R. R. Schmidt, Angew. Chem. Int. Ed. Engl. 1986, 25, 212-235.
20. R. U. Lemieux, Methods Carbohydr. Chem. 1963, 2, 223-234.
21. K. Ajisaka, H. Fujimoto, Carbohydr. Res. 1990, 199, 227-234.
22. B. Lindberg, J. Lönngren Methods Enzymol. 1978, 50, 3-33.
23. P. J. Harris, R. J. Henry, A. B. Blakeney, B. A. Stone, Carbohydr. Res. 1984, 127, 59-73.
24. I. M. Sims, Phytochemistry 2003, 63, 351-359.
25. J. M. Sugihara, Adv. Carbohydr. Chem. 1953, 8, 1-44.
26. A. H. Haines, E. J. Sutcliffe, Carbohydr. Res. 1985, 138, 143-147.
27. D. M. Clode, W. A. Laurie, D. McHale, J. B. Sheridan, Carbohydr. Res. 1985, 139, 161-183.
28. D. Plusquellec, K. Baczko, C. Chauvin, P. Durand (Isochem, Fr.), Fr. Demande, FR 2670493 A1 19920619, 1992;
29. Chem. Abstr. 1993, 118, 124955.
30. D. Rolf, G. R. Gray, Carbohydr. Res. 1984, 131, 17-28.
31. D. H. Brauns, J. Am. Chem. Soc. 1925, 47, 1280-1284.
32. Y. V. Voznil, L. N. Kiokov, A. A. Galogan, Carbohydr. Res. 1984, 132, 339-341.