Effect of intramolecular hydrogen-bonding network on the relative reactivities of carbohydrate OH groups

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 4, 1999, Pages 465-473

  Kurahashi, Takuya ^a   Mizutani, Tadashi ^a   Yoshida, Jun Ichi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002330018     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a808798i     Document Type: Article

References (20)

1. See, for example: Carbohydrate Recognition in Cellular Function, ed. G. Bock, and S. Harnett, Ciba Foundation Symposium 145, Wiley, New York, 1989.
2. S. Takayama, G. J. McGarvey, and C.-H. Wong, Client. Soc. Rev., 1997,26,407.
3. See, for example: S. Hanessian, Preparative Carbohydrate Chemistry, Marcel Dekker, New York, 1997.
4. C.-H. Wong, X.-S. Ye, and Z. Zhang, J. Am. Chem. Soc., 1998,120, 7137.
5. (a) S. David, and S. Hanessian, Tetrahedron, 1985, 41, 643; (b) K. Oshima, E. Kitazono, and Y. Aoyama, Tetrahedron Lett., 1997, 38,5001.
6. (a) J. M. Sugihara, Adv. Carbohydr. Chem. Biochem., 1953, 8, 1; (6) A. H. Haines, Adv. Carbohydr. Chem. Biochem., 1976, 33, 11; (c) Y. Tsuda, and K. Yoshimoto, J. Synth. Org. Chem. Jpn., 1984,42, 479.
7. C. Guibourdenche, J. Podlech, and D. Seebach, Liebigs Ann., 1996, 1121.
8. T.-H. Tang, D. M. Whitfield, S. P. Douglas, J. J. Krepinsky, and I. G. Csizmadia, Can. J. Chem., 1992, 70, 2434; 1994, 72, 1803; D. M. Whitfield, S. P. Douglas, T.-H. Tang, I. G. Csizmadia, H. Y. S. Pang, F. L. Moolten, and J. J. Krepinsky, Can. J. Clicm., 1994, 72, 2225.
9. (a) M. E. Brewster, M. Huane, E. Pop, J. Pitha, M. J. S. Dewar, J. J. Kaminski, and N. Bodor, Carbohydr. Rcs., 1993, 242, 53;
10. (b) S. Houdier, and S. Pérez, J. Carbohydr. Cliem., 1995,14, 1117.
11. T. Kawabata, M. Nagato, K. Takasu, and K. Fuji, J. Am. Client. Soc., 1997,119, 3169; S. J. Miller, G. T. Copeland, N. Papaioannou, T. E. Horstmann, and E. M. Ruel.J. Am. Cliem. Soc., 1998,120,1629.
12. See, for example: K. Ishihara, H. Kurihara, and H. Yamamoto, J. Org. Chem., 1993,58, 3791.
13. R. P. Bonar-Law, and J. K. M. Sanders, J. Am. Chem. Soc., 1995, 117,259.
14. R. W. Binkley, Modem Carbohydrate Chemistry, Marcel Dekker, New York, 1988, p. 143.
15. S. Yamabe, T. Minato, and Y. Kawabata, Can. J. Chem., 1984, 62, 235.
16. P. Hubbard, and W. J. Brittain, J. Org. Chem., 1998, 63, 677.
17. M. J. S. Dewar, and K. M. Dieter, J. Am. Chem. Soc., 1986, 108, 8075.
18. F. Mohamadi, N. G. J. Richards, W. C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W. C. Still, J. Comput. Chem., 1990,11,440.
19. J. J. P. Stewart, J. Comput. Chem., 1989,10, 209,221.
20. T. Mizutani, T. Kurahashi, T. Murakami, N. Matsumi, and H. Ogoshi, J. Am. Chem. Soc., 1997,119, 8991.