A Highly Practical Synthesis of Sulfated Lewis X: One-Pot, Two-Step Glycosylation Using "Armed/Disarmed" Coupling and Selective Benzoylation and Sulfation

Journal of Organic Chemistry

Volumn 62, Issue 20, 1997, Pages 6876-6881

  Tsukida, Takahiro ^a   Yoshida, Masahiro ^a   Kurokawa, Kiriko ^a   Nakai, Yoshiyuki ^a   Achiha, Toshio ^a   Kiyoi, Takao ^a   Kondo, Hirosato ^a  

^a KANEBO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000936475     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970076m     Document Type: Article

References (50)

1. (a) Bevilacqua, M. P.; Pober, J. S.; Mendrick, D. L.; Cotran, R. S.; Gimbrone, M. A.; Proc. Natl. Acad. Soc. U.S.A. 1987, 84, 9238-9242.
2. (b) Luscinskas, F. W.; Brock, A. F.; Arnaut, M. A.; Gimbrone, M. A. J. Immunol. 1989, 142, 2257-2263.
3. (c) Kuijpers, T. W.; Hakkert, B. C.; Hoogerwerf, M.; Leuuwenberg, J. F. M.; Roos, D. J. Immunol. 1991, 147, 1369-1376.
4. (d) Cummings, R. D.; Smith, D. F. BioEssays 1992, 14, 849-856.
5. (e) McEver, R. P. Curr. Opin. Immunol. 1994, 6, 75-84.
6. (a) Phillips, M. L.; Nudelman, E.; Gaeta, F. C. A.; Ferez, M.; Singhal, A. K.; Hakomori, S.-T.; Paulson, J. C. Science 1990, 250, 1130-1132.
7. (b) Walz, G.; Aruffo, A.; Kolanus, W.; Bevilacqua, M.; Seed, B. Science 1990, 250, 1132-1135.
8. (a) Nicolaou, K. C.; Hummel, C. W.; Bockovich, N. J.; Wong, C. H. J. Chem. Soc., Chem. Commun. 1991, 10, 870-872.
9. (b) Dumas, D. P.; Ichikawa, Y.; Wong, C.-H.; Lowe, J. B.; Rajan, P. N. Bioorg, Med. Chem. Lett. 1991, 1, 425-428.
10. (c) Nicolaou, K. C.; Hummel, C. W.; Iwabuchi, Y. J. Am. Chem. Soc. 1992, 114, 3126-3128.
11. (d) Ichikawa, Y.; Lin, Y.-C.; Dumas, D. P.; Shen, G.-J.; Garcia-Juncenda, E.; Williams, M. A.; Bayer, R.; Ketcham, C.; Walker, L. E.; Paulson, J. C.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 9283-9298.
12. (e) Danishefsky, S. J.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Koseki, K.; Oriyama, T.; Griffith, D. A.; Wong, C.-H.; Dumas, D. P. J. Am. Chem. Soc. 1992, 114, 8329-8331.
13. (f) Danishefsky, S. J.; Koseki, K.; Griffith, D. A.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Oriyama, T. J. Am. Chem. Soc. 1992, 114, 8331-8333.
14. (g) Danishefsky, S. J.; Gervay, J.; Peterson, J. M.; McDonald, F. E.; Koseki, K.; Griffith, D. A.; Oriyama, T.; Marsden, S. P. J. Am. Chem. Soc. 1995, 117, 1940-1953.
15. (a) Kondo, H.; Ichikawa, Y.; Wong, C.-H. J. Am. Chem. Soc. 1992, 114, 8748-8750.
16. (b) Halcomb, R. L.; Huang, H.; Wong, C.-H. J. Am. Chem. Soc. 1994, 116, 11315-11322.
17. (c) Ramphal, J. Y.; Zheng, Z.-L.; Ferez, C.; Walker, L. E.; DeFrees, S. A.; Gaeta, F. C. A. J. Med. Chem. 1994, 37, 3459-3463.
18. (a) Hasegawa, A.; Ito, K.; Ishida, H.; Kiso, M. J. Carbohydr, Chem. 1995, 14, 353-368.
19. (b) Yuen, C. T.; Lawson, A. M.; Chai, W.; Larkin, M.; Stoll, M. S.; Stuart, A. C.; Sullivan, F. X.; Ahern, T. J.; Feizi, T. Biochemistry 1992, 31, 9126-9131.
20. (c) Nicolaou, K. C.; Bockovich, N. J.; Carcanague, D. R. J. Am. Chem. Soc. 1993, 115, 8843-8844.
21. (d) Lubineau, A.; Le Gallic, J.; Lemoine, R. J. Chem. Soc., Chem. Commun. 1993, 1419-1420.
22. Ohmoto, H.; Nakamura, K.; Inoue, T.; Kondo, N.; Inoue, Y.; Yoshino, K.; Kondo, H.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Med. Chem. 1996, 39, 1339-1343.
23. Dasgupta, F.; Rao, B. N. N. Exp. Opin. Invest. Drugs 1994, 3, 709-724.
24. Wada, Y.; Saito, T.; Matsuda, N.; Ohmoto, H.; Yoshino, K.; Ohashi, M.; Kondo, H.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Med. Chem. 1996, 39, 2055-2059.
25. Tsujishita, H.; Hiramatsu, Y.; Kondo, N.; Ohmoto, H.; Kondo, H.; Kiso, M.; Hasegawa, A. J. Med. Chem. 1997, 40, 362-369.
26. 3) δ1.26 (s, 3H), 1.40 (s, 3H), 3.07-3.14 (m, 1H), 3.20-3.37 (m, 4H), 3.54-3.64 (m, 3H), 3.74-3.86 (m, 2H), 3.95-4.0 (t, 1H, J=7.0 Hz), 4.12 (dd, 1H, J = 1.5, 7.1Hz), 4.30 (dd, 2H, J = 8.0, 9.3 Hz), 4.58 (d, 1H, J = 12.2 Hz), 4.83 (d, 1H, J = 12.2 Hz), 7.26-7.41 (m, 5H).
27. 3CN = 1:5), retention time (min); 4.5 for compound 5a, 5.7 for compound 7a, 9.0 for compound 6a, 11.2 for compound 8a.
28. Nagao, Y.; Nukada, T.; Ikeda, K.; Achiwa, K. Chem. Pharm. Bull 1995, 43, 1536-1542.
29. (a) Mootoo, D. R.; Konradsson, P.; Udodong, U. E.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583-5584.
30. (b) Fraser-Reid, B.; Wu, Z.; Udodong, U. E.; Ottosson, H. J. Org. Chem. 1990, 55, 6068-6070.
31. (c) Fraser-Reid, B.; Udodong, U. E.; Wu, Z.; Ottoson, H.; Merritt, R.; Rao, C. S.; Roberts, C. Synlett 1992, 927-942.
32. (d) Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1990, 270-272.
33. (e) Konradsson, P.; Udodong, U.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313-4316.
34. (f) Konradsson, P.; Fraser-Reid, B. J. Chem. Soc. Chem. Commun. 1989, 1124-1125.
35. (g) Roberts, C.; Madsen, R.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 1546-1553.
36. (h) Fraser-Reid, B.; Wu, Z.; Andrews, C. W.; Skowronski, E.; Bowen, J. P. J. Am. Chem. Soc. 1991, 223, 1434-1435.
37. (i) Madsen, R.; Udodong, U.; Roberts, C.; Mootoo, D.; Mootoo, U. D. R.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1995, 117, 1554-1565.
38. (j) Boons, G.-J. Tetrahedron 1996, 52, 1095-1121.
39. (a) Veeneman, G. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 275-278.
40. (b) Boons, G.-J.; Grice, P.; Leslie, R.; Ley, S. U.; Yeung, L. L. Tetrahedron Lett. 1993, 34, 8523-8526.
41. (c) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331-1334.
42. (d) Zuurmond, H. M.; van der Laan, S. C.; van der Marel, G. A.; van Boom, J. H. Carbohydr. Res. 1991, 275, C1.
43. (a) Raghavan, S.; Kahne, D. J. Am. Chem. Soc. 1993, 115, 1580-1581.
44. (b) Yamada, H.; Harada, T.; Takahashi, T. J. Am. Chem. Soc. 1994, 116, 7917-7919.
45. (c) Ley, S. V.; Priepke, H. W. M. Angew. Chem., Int. Ed. Engl. 1994, 33, 2292-2294.
46. Guilbert, B.; Davis, N. J.; Flitsch, S. L. Tetrahedron Lett. 1994, 35, 6563-6566.
47. Kameyama, A.; Ishida, H.; Kiso, M.; Hasegawa, A. J. Carbohydr. Chem. 1991, 10, 549-560.
48. Lemieux, R. U.; Driguez, H. J. Am. Chem. Soc. 1975, 97, 4069-4075.
49. Komba, S.; Ishida, H.; Kiso, M.; Hasegawa, A. Carbohydr, Res. 1996, 285, C1-C8.
50. Ladish, S.; Hasegawa, A.; Li, R.; Kiso, M. Biochem. Biophys. Res. Commun. 1994, 203, 1102-1109.