Skip to main content
Log in

Glycosylation of cardenolides. IV. Strophanthidin 5-α-L-rhamnoside and 3,5-bisglycosides

  • Published:
Chemistry of Natural Compounds Aims and scope

Summary

1. The Koenigs-Knorr condensation of acetobromorhamnose with strophanthidin acetate has given strophanthidin L-rhamnoside substituted at the C5 hydroxyl, and its condensation with free strophanthidin has given strophanthidin di-α-O-rhamnoside substituted at the C3 and C5 hydroxy groups.

2. Under similar conditions, methyl 2,3,4-tri-O-acetyl-l-bromo-1-deoxy-α-D-galacturonate and strophanthidin have given the corresponding strophanthidin diglycoside substituted at the C3 and C5 hydroxyls.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

  1. R. M. Carman, R. G. Coombe, and T. R. Watson, Aust. J. Chem.,17, 573 (1964).

    Article  CAS  Google Scholar 

  2. H. Lichti, P. Niklaus, and A. Wartburg, Helv. Chim. Acta,56, 2083, 2088 (1973).

    Article  CAS  Google Scholar 

  3. I. F. Makarevich, Khim. Prirodn. Soedin.,191 (1969).

  4. I. F. Makarevich, S. G. Kislichenko, D. G. Kolesnikov, A. Ya. Topchii, and M. A. Angarskaya, Khim. Prirodn. Soedin., 45 (1971).

  5. V. T. Chernobai, Zh. Obshch. Khim.,34, 1690 (1964).

    CAS  Google Scholar 

  6. W. W. Zorbach and K. V. Bhat, Adv. Carbohyd. Chem.,22, 273 (1966); K. Takiura, H. Yuki, Y. Okamoto, H. Takai, and S. Honda, Chem. Pharm. Bull.,22, 2263 (1974).

    Google Scholar 

  7. V. T. Chernobai, Zh. Obshch. Khim.,34, 1018 (1964).

    CAS  Google Scholar 

  8. K. Reule and T. Reichstein, Helv. Chim. Acta,35, 98 (1952).

    Article  Google Scholar 

  9. R. N. Jones, P. Humphries, F. Herling, and K. Dobriner, J. Am. Chem. Soc.,73, 3215 (1951).

    Article  CAS  Google Scholar 

  10. C. Ingold, Structure and Mechanism in Organic Chemistry, second Ed., Cornell Univ. Press, Ithaca, New York (1969).

    Google Scholar 

  11. Ya. V. Rashkes, M. B. Gorovits, G. K. Makarichev, and N. K. Abubakirov, Khim. Prirodn. Soedin., 747 (1971).

  12. Ya. V. Rashkes, Khim. Prirodn. Soedin., 126 (1973).

  13. W. Klyne, Biochem. J.,47, No. 4 xli (1950).

    CAS  Google Scholar 

  14. E. Fischer, M. Bergmann, and A. Rabe, Ber.,53, 2362 (1920).

    Google Scholar 

  15. N. K. Kochetkov, Methods of Carbohydrate Chemistry [in Russian], Moscow (1967), p. 124.

  16. S. Morell, L. Baur, and K. P. Link, J. Biol. Chem.,110, 719 (1935).

    CAS  Google Scholar 

  17. J. Becker, Biochim. Biophys. Acta,100, 574 (1965).

    Article  CAS  Google Scholar 

  18. N. Sh. Pal'yants, A. F. Bochkov, N. K. Abubakirov, Khim. Prirodn. Soedin., 58 (1976).

  19. N. Sh. Pal'yants, M. B. Gorovits, and N. K. Abubakirov, Khim. Prirodn. Soedin., 263 (1975).

Download references

Authors

Additional information

Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 6, pp. 765–772, November–December, 1976.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pal'yants, N.S., Gorovits, M.V. & Abubakirov, N.K. Glycosylation of cardenolides. IV. Strophanthidin 5-α-L-rhamnoside and 3,5-bisglycosides. Chem Nat Compd 12, 687–692 (1976). https://doi.org/10.1007/BF00564960

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00564960

Keywords

Navigation