Stereoselective α-sialylation with sialyl xanthate and phenylsulfenyl triflate as a promotor

Journal of Organic Chemistry

Volumn 61, Issue 5, 1996, Pages 1702-1706

  Martichonok, Valeri ^a   Whitesides, George M ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000331272     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951711w     Document Type: Article

References (43)

1. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
2. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
3. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
4. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
5. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
6. Schauer, R. Adv. Carbohydr. Chem. Biochem. 1982, 40, 131. Hakomori, S. I. Annu. Rev. Immunol. 1984, 307, 560. Ravindranath, M. H.; Higa, H. H.; Cooper, E. L.; Paulson, J. C. J. Biol. Chem. 1985, 260. 8850. Paulson, J. C. Interactions of Animal Viruses with Cell Surface Receptors: Conn, P. M., Ed.; Academic Press: New York, 1985; p 131. Savage, D. C. Effect on Host Animals of Bacteria Adhering to Epithelial Surfaces; Savage, D. C., Fletcher, M., Eds.; Plenum Press: New York, 1985; p 437. Shibuya, N.; Goldstein, I. J.; Broekaert, W. F ; Nsimba-Lubaki, M.; Peeters, B.; Peumans, W. J. J. Biol. Chem. 1987, 262, 1596.
7. Karlsson, K.-A. Molecular Mechanisms of Microbial Adhesion; Springer-Verlag: New York, 1988; pp 77-96.
8. Sharon, N.; Lis, H. Science 1989, 246, 227-234. Paulson, J. C. The Receptors; Academic Press: New York, 1985; pp 131-219.
9. Sharon, N.; Lis, H. Science 1989, 246, 227-234. Paulson, J. C. The Receptors; Academic Press: New York, 1985; pp 131-219.
10. Springer, T A.; Lasky, L. A. Nature 1991, 349, 196-197. Paulson, J. C. Adhesion: Its Role in Inflammatory Disease; Stockton Press: New York. 1992; pp 19-42. Crocker, P. R.; Kelm, S.; Dubois, C.; Martin, B.: McWilliam, A. S.; Shotton, D. M.; Paulson, J. C.; Gordon, S. EMBO J. 1991, 10, 1661-1669.
11. Springer, T A.; Lasky, L. A. Nature 1991, 349, 196-197. Paulson, J. C. Adhesion: Its Role in Inflammatory Disease; Stockton Press: New York. 1992; pp 19-42. Crocker, P. R.; Kelm, S.; Dubois, C.; Martin, B.: McWilliam, A. S.; Shotton, D. M.; Paulson, J. C.; Gordon, S. EMBO J. 1991, 10, 1661-1669.
12. Springer, T A.; Lasky, L. A. Nature 1991, 349, 196-197. Paulson, J. C. Adhesion: Its Role in Inflammatory Disease; Stockton Press: New York. 1992; pp 19-42. Crocker, P. R.; Kelm, S.; Dubois, C.; Martin, B.: McWilliam, A. S.; Shotton, D. M.; Paulson, J. C.; Gordon, S. EMBO J. 1991, 10, 1661-1669.
13. Ito, Y.; Gaudino, J. J.; Paulson, J. C. Pure Appi. Chem. 1993, 65, 753-762 DeNinno, M. P. Synthesis 1991, 583-593.
14. Ito, Y.; Gaudino, J. J.; Paulson, J. C. Pure Appi. Chem. 1993, 65, 753-762 DeNinno, M. P. Synthesis 1991, 583-593.
15. Wong, C.-H.; Whitesides, G. M. Enzymes in Synthetic Organic Chemistry; Pergamon: New York, 1994.
16. Birberg, W.; Lonn, H. Tetrahedron Lett. 1991, 32, 7453-7456. Lonn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277-281. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 118, 1616-1634. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11, 699-714.
17. Birberg, W.; Lonn, H. Tetrahedron Lett. 1991, 32, 7453-7456. Lonn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277-281. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 118, 1616-1634. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11, 699-714.
18. Birberg, W.; Lonn, H. Tetrahedron Lett. 1991, 32, 7453-7456. Lonn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277-281. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 118, 1616-1634. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11, 699-714.
19. Birberg, W.; Lonn, H. Tetrahedron Lett. 1991, 32, 7453-7456. Lonn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277-281. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 118, 1616-1634. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11, 699-714.
20. Birberg, W.; Lonn, H. Tetrahedron Lett. 1991, 32, 7453-7456. Lonn, H.; Stenvall, K. Tetrahedron Lett. 1992, 33, 115-116. Hasegawa, A.; Ohki, H.; Nagahama, T.; Ishida, H.; Kiso, M. Carbohydr. Res. 1991, 212, 277-281. Sabesan, S.; Neira, S.; Davidson, F.; Duus, J.; Bock, K. J. Am. Chem. Soc. 1994, 118, 1616-1634. Hasegawa, A.; Nagahama, T.; Ohki, H.; Kiso, M. J. Carbohydr. Chem. 1992, 11, 699-714.
21. Fugedi, P.; Garegg, P. J. Carbohydr. Res. 1986, 149, C9-C12. Ravenscroft, M.; Roberts, R. M. G.; Tillett, J. G. J. Chem. Soc., Perkin Trans. 2 1982, 1569-1572.
22. Fugedi, P.; Garegg, P. J. Carbohydr. Res. 1986, 149, C9-C12. Ravenscroft, M.; Roberts, R. M. G.; Tillett, J. G. J. Chem. Soc., Perkin Trans. 2 1982, 1569-1572.
23. Dasgupta, F.; Garegg, P. J. Carbohydr. Res. 1988, 177, C13-C17.
24. Liebe, B.; Kunz, H. Tetrahedron Lett. 1994, 35, 8777-8778
25. (b) Marra, A.; Sinay. P. Carbohydr. Res. 1990, 195, 303-308.
26. Marra, A.; Sinay, P. Carbohydr. Res. 1989, 187, 35-42.
27. Thea, S.; Cevasco, G. Tetrahedron Lett. 1988, 29, 2865-2866.
28. Kuhle, E. The Chemistry of the Sulphenic Acids; Georg Thieme Publishers: Stuttgart. 1973.
29. Okamoto, K.; Kondo, T.; Goto, T. Bull. Chem. Soc. Jpn. 1987, 60, 637-643.
30. Hori, H.; Nakajima, T.; Nishida, Y.; Ohmi, H.; Meguro, H. Tetrahedron Lett. 1988, 29, 6317-6320.
31. Dabrowski, U.; Friebolin, H.; Brossmer, R.; Supp, M. Tetrahedron Lett. 1979, 48, 4637-4640.
32. Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans, 1 1990, 747-750. Schmidt, R. R; Behrendt, M.; Toepfer. A. Synlett 1990. 694-696 Braccini, I.; Derouet C.; Esnault, J.; Hervé du Penhoat, C.: Mallet, J.-.M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246. 23-41.
33. Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans, 1 1990, 747-750. Schmidt, R. R; Behrendt, M.; Toepfer. A. Synlett 1990. 694-696 Braccini, I.; Derouet C.; Esnault, J.; Hervé du Penhoat, C.: Mallet, J.-.M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246. 23-41.
34. Ratcliffe, A. J.; Fraser-Reid, B. J. Chem. Soc., Perkin Trans, 1 1990, 747-750. Schmidt, R. R; Behrendt, M.; Toepfer. A. Synlett 1990. 694-696 Braccini, I.; Derouet C.; Esnault, J.; Hervé du Penhoat, C.: Mallet, J.-.M.; Michon, V.; Sinay, P. Carbohydr. Res. 1993, 246. 23-41.
35. Stewart, J. J. P. J. Comput. Chem 1989, 10, 209-220. Stewart. J. J. P. J. Comput. Chem 1989, 10, 221-264. PM3 was used from within MOPAC 6.0 (QCPE 455).
36. Stewart, J. J. P. J. Comput. Chem 1989, 10, 209-220. Stewart. J. J. P. J. Comput. Chem 1989, 10, 221-264. PM3 was used from within MOPAC 6.0 (QCPE 455).
37. Perin, D. D.; Armarego, W. L. F.; Pen-in. D. R. Purification of Laboratory Chemicals; Pergamon Press: New York, 1980.
38. Roy, R.; Laferriere, C. A, Can. J. Cfiem. 1990, 68, 2045-2054.
39. Kuhn, R.; Lutz, P.; MacDonald, D L. Chem. Ber. 1966, 99, 611-617.
40. Paulsen, H.; Hasenkamp, T.; Paal, M. Carbohydr. Res. 1985, 144, 45-55.
41. Jansson, K.; Ahlfors, S.; Frejd, T.; Kihlberg, J.; Magnusson, G.; Dahmen, J.; Noori, G.; Stenvall, K. J. Org. Chem. 1988, 53, 5629-5647.
42. Damshefsky, S. J.; Gervay, J.; Peterson, J. M.; Mcdonald, P. E.; Koseki. K; Griffith, D. A.; Oriyama, T.; Mareden, S. P. J. Am Chem. Soc. 1995, 117, 1940-1953.
43. Almasi, L; Hanz, A. Chem Ber. 1961, 94, 725-728.