Hydrolysis of α- and β-Glycosides. New Experimental Data and Modeling of Reaction Pathways

Organic Letters

Volumn 6, Issue 4, 2004, Pages 505-508

  Deslongchamps, Pierre ^a,b   Li, Shigui ^a,b   Dory, Yves L ^c  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

^b Lab de Synthèse Organique   (Canada)

^c Lab de Synt Supramoleculaire   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; GLYCOSIDE; METHANOL; OXYGEN;

ARTICLE; CALCULATION; CHEMICAL BOND; CYCLIZATION; HYDROLYSIS; REACTION ANALYSIS;

CATALYSIS; GLYCOSIDES; HYDROLYSIS; INDICATORS AND REAGENTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; STEREOISOMERISM; THERMODYNAMICS;

EID: 1342311504     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol036220+     Document Type: Article

References (34)

1. Walsh, C. Enzymatic Reaction Mechanisms; W. H. Freeman: San Francisco, CA, 1979.
2. Ford, L. O.; Johnson, L. N.; Machin, P. A.; Phillips, D. C.; Tjian, R. J. Mol. Biol. 1974, 88, 349.
3. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry; Pergamon Press: Oxford, England, 1983.
4. Cordes, E. H. Prog. Org. Chem. 1967, 4, 1.
5. Kirby, A. J. Acc. Chem. Res. 1985, 17, 305.
6. Post, C. B.; Karplus, M. J. Am. Chem. Soc. 1986, 108, 1317.
7. (a) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: New York, 1983.
8. (b) Cordes, E. H.; Bull, H. G. Transition State in Biochemical Processes; Gandour, D. R., Schowen, R. L., Eds.; Plenum: New York, 1978.
9. (c) BeMiller, J. N.; Doyle, E. R. Carbohydr. Res. 1971, 20, 23.
10. (a) Warshell, A.; Levitt, M. J. Mol. Biol. 1976, 103, 227.
11. (b) Pincus, M. R.; Scheraga, H. A. Macromolecules 1979, 12, 633.
12. Gupta, R. B.; Franck, R. W. J. Am. Chem. Soc. 1987, 109, 6554.
13. (a) Angibeaud, P.; Utille, J.-P. J. Chem. Soc., Perkin Trans, 1 1990, 1490.
14. (b) McPhail, D. R.; Lee, J. R.; Fraser-Reid, B. J. Am. Chem. Soc. 1992, 114, 1905.
15. (c) Dasgupta, F.; Singh, P. P.; Srivastava, H. C. Indian J. Chem. 1988, 27B, 527.
16. (d) Guindon, Y.; Anderson, P. C. Tetrahedron Lett. 1987, 28, 2485.
17. (e) Lichtenthaler, F. W.; Breunig, I.; Fisher, W. Tetrahedron Lett. 1971, 2825.
18. Deslongchamps, P. In The Anomeric Effect and Associated Stereo-electronic Effects; Thatcher, G. R. J., Ed.; ACS Symp. Ser. No. 539; American Chemical Society: Washington, DC, 1993.
19. (a) Salzner, U.; Schleyer, P. v. R. J. Org. Chem. 1994, 59, 2138.
20. (b) Mohr, M.; Bryce, R. A.; Millier, I. J. Phys. Chem. A 2001, 705, 8216.
21. (a) Li, S.; Kirby, A. J.; Deslongchamps, P. Tetrahedron Lett. 1993, 34, 7757.
22. (b) Ratcliffe, A. J.; Mootoo, D. R.; Webster, C.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 7661.
23. (a) Deslongchamps, P.; Dory, Y. L.; Li, S. Can. J. Chem. 1994, 72, 2021.
24. (b) Eikeren, E. V. J. Org. Chem. 1980, 45, 4641.
25. Ishii, T.; Ishizu, A.; Nakano, J. Carbohydr. Res. 1976, 48, 33.
26. (a) McClelland, R. A.; Watada, B.; Lew, C. S. Q. J. Chem. Soc., Perkin Trans. 2 1993, 1723.
27. (b) Kresge, A. J.; Chwang, W. K. J. Am. Chem. Soc. 1978, 100, 1249.
28. Mootoo, D. R.; Date, V.; Fraser-Reid, B. J. Chem. Soc., Chem. Commun. 1987, 1862.
29. Li, S.; Dory, Y. L.; Deslongchamps, P. Tetrahedron 1996, 52, 14841.
30. Kresge, A. J.; Weeks, D. P. J. Am. Chem. Soc. 1984, 106, 7140.
31. Bürgi, H. B.; Dunitz, J. D.; Shefter, E. J. Am. Chem. Soc. 1973, 95, 5065.
32. Andrews, C. W.; Fraser-Reid, B.; Bowen, J. P. J. Am. Chem. Soc. 1991, 113, 8293.
33. Liras, J. L.; Anslyn, E. V. J. Am. Chem. Soc. 1994, 116, 2645.
34. Franck, R. W. Bioorg. Chem. 1992, 20, 77.