Skip to main content
SpringerLink
Log in

Reaction of cholesterol with acetylated alkyl orthoacetates of D-glucopyranose

  • Published:
Chemistry of Natural Compounds Aims and scope

Summary

The condensation of acetylated alkyl orthoacetates of D-glucose with cholesterol has been studied. It has been shown that either transesterification or glycosylation may take place, according to the reaction conditions. Conditions have been found under which the sole direction of the reaction is glycosylation, leading to the 1, 2-trans-glycoside. A standard method for glycosylating complex alcohols with sugar orthoesters has been proposed.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, Izv. AN SSSR, ser. khim., 2234, 1963.

  2. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, Tetrah. let., 289, 1964.

  3. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, DAN SSSR, 161, 1342, 1965.

    CAS  Google Scholar 

  4. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, DAN SSSR, 162, 104, 1965.

    CAS  Google Scholar 

  5. N. K. Kochetkov et al., Izv. AN SSSR, ser. khim., 1698, 1965.

  6. H. G. Bott, W. N. Haworth, and E. L. Hirst, J. Chem. Soc., 1395, 1930.

  7. R. U. Lemieux, Adv. Carb. Chem., 9, 1, 1954.

    Article  CAS  Google Scholar 

  8. B. Helferich and K. Weiss, Chem. Ber., 89, 314, 1956.

    Article  CAS  Google Scholar 

  9. A. Ya. Khorlin and A. F. Bochkov, Izv. AN SSSR, OKhN, 1120, 1962.

  10. A. Ya. Khorlin, A. F. Bochkov, and N. K. Kochetkov, Izv. AN SSSR, ser. khim., 2214, 1966.

  11. Ch. Meyster and K. Miescher, Helv. Chem. Acta., 27, 231, 1944.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Institute of the Chemistry of Natural Compounds AS USSR, USSR

    A. Ya. Khorlin, A. F. Bochkov & N. K. Kochetkov

Authors
  1. A. Ya. Khorlin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. F. Bochkov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. N. K. Kochetkov
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

Khimiya Prirodnykh Soedinenii, Vol. 2, No. 1, pp. 6–12, 1966

Rights and permissions

Reprints and permissions

About this article

Cite this article

Khorlin, A.Y., Bochkov, A.F. & Kochetkov, N.K. Reaction of cholesterol with acetylated alkyl orthoacetates of D-glucopyranose. Chem Nat Compd 2, 4–8 (1966). https://doi.org/10.1007/BF00566589

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00566589

Keywords

Search

Navigation