Cyclodextrin Derivatisation: Directed Reaction of Silylated Intermediates

  • R. L. Wife
  • D. E. Reed
  • H. C. Volger
Conference paper
Part of the Advances in Inclusion Science book series (AIS, volume 1)


Methods for the complete or partial (selective) silylation of β-cyclodextrin are described that provide intermediates for further derivatisation. The procedure is useful in directing reaction to previously functionalised centres affording material that is soluble in organic solvents, facilitating chromatographic separations and making possible structural assignments for the product macromolecules by proton NMR spectroscopy.

The method is applied to the sequential attachment and attempted capping of β-cyclodextrin by a porphyrin template. The product conjugate was found to be hydrolytically unstable. Representative proton NMR spectra for a series of silyl derivatives and intermediates are analysed to demonstrate further the advantage of the method.


Oxalyl Chloride Fluoride Anion Mild Acid Hydrolysis Ethyl Bromoacetate Silyl Derivative 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature Cited

  1. 1.
    Bender, M.L., Koniyama, M.: Cyclodextrin Chemistry, Springer-Verlag, Berlin-Heidelberg-New York 1978.Google Scholar
  2. 2.
    Saenger, W.: Angew. Chem. Int. Ed. Eng. 19 344, /1980/CrossRefGoogle Scholar
  3. 3.
    Horikoshi, K.: Process Biochem. 26, /1979/Google Scholar
  4. 4.
    Breslow, R.: Isr. J. Chem. 18 187, /1979/Google Scholar
  5. 5.
    Boger, J., Brenner, D.G., Knowles, J.R.: J. Am. Chem. Soc. 101 7631, /1979/CrossRefGoogle Scholar
  6. 6.
    Tabushi, I., Kuroda, Y., Mochizuki, A.: J. Am. Chem. Soc. 102 1152, /1980/CrossRefGoogle Scholar
  7. 7.
    Breslow, R., Hammond, M., Lauer, M.: J. Am. Chem. Soc. 102 421, /1980/CrossRefGoogle Scholar
  8. 8.
    Siegel, B., Breslow, R.: J. Am. Chem. Soc. 97 6869, /1975/CrossRefGoogle Scholar
  9. 9.
    Bergeron, R.J., Meeley, M.P.: Bioorg. Chem. 5 121, /1976/CrossRefGoogle Scholar
  10. 10.
    Boger, J., Corcoran, R.J., Lehn, J.M.: Helv. Chim. Acta. 61 2190, /1978/CrossRefGoogle Scholar
  11. 11.
    Iwakura, Y., Uno, K., Toda, F., Onozuka, S., Hattori, K., Bender, M.L.: J. Am. Chem. Soc., 97 4432, /1975/CrossRefGoogle Scholar
  12. 12.
    Onozuka, S., Kojima, M., Hattori, K., Toda, F.: Bull. Chem. Soc. Jpn. 53 3221, /1980/CrossRefGoogle Scholar
  13. 13.
    Tabushi, I., Kuroda, Y., Yokota, K., Yuan, L.C.: J. Am. Chem. Soc. 103 711, /1981/ and references therein.CrossRefGoogle Scholar
  14. 14.
    Melton, L.D., Slessor, K.N.: Carbohydr. Res. 18 29, /1971/CrossRefGoogle Scholar
  15. 15.
    Chao, Y., PhD Thesis, Columbia University, New York 1973Google Scholar
  16. 16.
    Matsui, Y., Okimoto, A.: Bull. Chem. Soc. Jpn. 51 3030, /1978/CrossRefGoogle Scholar
  17. 17.
    Beadle, J.B.: J. Chromatogr. 42 201, /1969/CrossRefGoogle Scholar
  18. 18.
    Walton, D.R.M., Private communication.Google Scholar
  19. 19.
    Tabushi, I., Shimizu, N., Sugimoto, T., Shiozuka, M., Yamamura, K.: J. Am. Chem. Soc. 99 7100, /1977/; Matsui, T., Yokoi, T., Mochida, K.; Chem. Lett. 1037, /1976/CrossRefGoogle Scholar
  20. 19a.
    Matsui, T., Yokoi, T., Mochida, K.; Chem. Lett. 1037, /1976/Google Scholar
  21. 20.
    Corey, E.J., Venkateswarlu, A.: J. Am. Chem. Soc. 94 6190, /1972/CrossRefGoogle Scholar
  22. 21.
    Hunt, B.J., Rigby, W.: Chem. & Ind. 1868, /1967/Google Scholar

Copyright information

© Springer Science+Business Media Dordrecht 1982

Authors and Affiliations

  • R. L. Wife
    • 1
  • D. E. Reed
    • 1
  • H. C. Volger
    • 1
  1. 1.Shell Biosciences LaboratorySittingbourneEngland

Personalised recommendations