Selective activation of glycosyl donors utilising electrochemical techniques: A study of the thermodynamic oxidation potentials of a range of chalcoglycosides

Organic and Biomolecular Chemistry

Volumn 2, Issue 15, 2004, Pages 2188-2194

  France, Robert R ^a   Rees, Neil V ^a   Wadhawan, Jay D ^a   Fairbanks, Antony J ^a   Compton, Richard G ^a  

^a UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ATMOSPHERIC PRESSURE; CYCLIC VOLTAMMETRY; DEGRADATION; ELECTROCHEMISTRY; FOURIER TRANSFORM INFRARED SPECTROSCOPY; GLYCOLS; IONIZATION; MASS SPECTROMETRY; OXIDATION; REACTION KINETICS; REDOX REACTIONS; SILICA; SYNTHESIS (CHEMICAL); THERMODYNAMICS; THIN LAYER CHROMATOGRAPHY;

ELECTRON TRANSFER; FLASH CHROMATOGRAPHY; REDOX POTENTIALS; THERMODYNAMIC OXIDATION;

CHEMICAL ACTIVATION;

TETRAO;

CATION; GLYCOSIDE; OLIGOSACCHARIDE;

ARTICLE; CHEMISTRY; ELECTROCHEMISTRY; KINETICS; METABOLISM; OXIDATION REDUCTION REACTION; THERMODYNAMICS;

CATIONS; ELECTROCHEMISTRY; GLYCOSIDES; KINETICS; OLIGOSACCHARIDES; OXIDATION-REDUCTION; THERMODYNAMICS;

EID: 4344592359     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b316720h     Document Type: Article

References (38)

1. A. Varki, Glycobiology, 1993, 3, 97.
2. R. A. Dwek, Chem. Rev., 1996, 96, 683.
3. B. G. Davis, J. Chem. Soc., Perkin Trans. 1, 2000, 2137.
4. D. R. Mootoo, P. Konradsson, U. Udodong and B. Fraser-Reid, J. Am. Chem. Soc., 1988, 110, 5583.
5. G. H. Veeneman and J. H. Van Boom, Tetrahedron Lett., 1990, 31, 274.
6. P. Grice, S. V. Ley, J. Pietruszka, H. W. M. Priepke and E. P. E. Walther, Synlett., 1995, 781.
7. N. L. Douglas, S. V. Ley, U. Lücking and S. L. Warriner, J. Chem. Soc., Perkin Trans. 1, 1998, 51.
8. Z. Zhang, I. R. Ollmann, X.-S. Ye, R. Wischnat, T. Baasov and C.-H. Wong, J. Am. Chem. Soc., 1999, 121, 734.
9. V. G. Mairanovsky, Angew. Chem., Int. Ed. Engl., 1976, 15, 281.
10. R. Noyori and I. Kurimoto, J. Org. Chem., 1986, 51, 4320.
11. C. Amatore, A. Jutand, J. M. Mallet, G. Meyer and P. Sinaÿ, J. Chem. Soc., Chem. Commun., 1990, 718.
12. G. Balavoine, A. Gref, J.-C. Fischer and A. Lubineau, Tetrahedron Lett., 1990, 40, 5761.
13. J. M. Mallet, G. Meyer, F. Yvelin, A. Jutand, C. Amatore and P. Sinaÿ, Carbohydr. Res., 1993, 244, 237.
14. G. Balavoine, S. Bertina, A. Gref, J. C. Fischer and A. Lubineau, J. Carbohydr. Chem., 1995, 8, 1217.
15. G. Balavoine, S. Bertina, A. Gref, J. C. Fischer and A. Lubineau, J. Carbohydr. Chem., 1995, 8, 1237.
16. S. Yamago, K. Kokubo and J. Yoshida, Chem. Lett., 1997, 111.
17. S. Yamago, K. Kokubo, O. Hara, S. Masuda and J. Yoshida, J. Org. Chem., 2002, 67, 8584.
18. R. R. France, R. G. Compton, B. G. Davis, A. J. Fairbanks, N. V. Rees and J. D. Wadhawan, Org. Biomol. Chem., 2004, DOI: 10.1039/ b316728c.
19. M. Rudolph and D. P. Reddy, Anal. Chem., 1994, 66, 589A.
20. A. J. Bard and L. R. Faulkner, Electrochemical Methods: Fundamentals and Applications, John Wiley, New York, 2001, 2nd edn., p. 231.
21. C. R. Wilke and P. Chang, AIChE J., 1955, 1, 261.
22. J. A. Alden, F. Hutchinson and R. G. Compton, J. Phys. Chem. B, 1997, 101, 949.
23. A. Kunai, J. Harada, J. Izumi, H. Tachihara and K. Sasaki, Electrochim. Acta, 1983, 28, 1361.
24. D. A. Johnson, Some Thermodynamic Aspects of Inorganic Chemistry, Cambridge University Press, Cambridge, UK, 1982, 2nd edn., p. 202.
25. Handbook of Chemistry and Physics, CRC Press, New York, 1995, 76th edn.
26. C. Amatore, C. Lefrou and F. Pfluger, J. Electroanal. Chem., 1989, 270, 43.
27. C. Amatore, E. Maisonhaute and G. Simmonneau, Electrochem. Commun., 2000, 2, 81.
28. C. Amatore, E. Maisonhaute and G. Simmonneau, J. Electroanal. Chem., 2002, 486, 141.
29. R. M. Wightman and D. O. Wipf, in Electroanalytical Chemistry, A. J. Bard, ed., Marcel Dekker, New York, 1989, vol. 15, p. 267.
30. R. Caputo, H. Kunz, D. Mastroianni, G. Palumbo, S. Pedatella and F. Solla, Eur. J. Org. Chem., 1999, 11, 3147.
31. R. V. Stick, D. Tilbrook, G. Matthew and S. J. Williams, Aust. J. Chem., 1997, 3, 233.
32. S. Mehta and B. M. Pinto, J. Org. Chem., 1993, 12, 3269.
33. K. C. Nicolaou, J. L. Randall and G. T. Furst, J. Am. Chem. Soc., 1985, 19, 5556.
34. R. J. Ferrier, R. W. Hay and N. Vethaviyasar, Carbohydr. Res., 1973, 27, 55.
35. J. W. Van Cleve, Carbohydr. Res., 1979, 70, 161.
36. E. M. Montgomary, N. K. Richtmyer and C. S. Hudson, J. Org. Chem., 1945, 11, 301.
37. K. Mori, Z.-H. Qian and S. Watanabe, Liebigs Ann. Chem., 1992, 5, 485.
38. K. Brewster, J. M. Harrison and T. O. Inch, Tetrahedron Lett., 1979, 52, 5051.