Skip to main content
Log in

Synthesis of aryl glycosides by ortho-ester method

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The ortho-ester method of glycoside preparation was used to prepare aryl glucosides.

  2. 2.

    The tetraacetates ofβ-naphthol, p-methoxyphenol, and p-hydroxyacetophenoneβ-D-glucopyranosides were synthesized.

  3. 3.

    The differences in the course of the condensation of sugar ortho-esters with phenols compared with alcohols were demonstrated.

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. W. Karrer, Konstitution und Vorkommen der Organischen Pflanzenstoffe, Basel (1958).

  2. J. B. Pridham, Advances Carbohydr. Chem.,20, 371 (1965).

    Google Scholar 

  3. J. Conchie, G. A. Levvy, and C. A. Marsh, Advances Carbohydr. Chem.,12, 157 (1957).

    Google Scholar 

  4. R. L. Whistler and M. L. Wolfrom, Methods of Carbohydrate Chemistry [Russian translation] (1967), pp. 174, 179.

  5. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, Tetrahedron Letters, 289 (1964).

  6. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, Tetrahedron,23, 693 (1967).

    Google Scholar 

  7. N. K. Kochetkov, A. Ya. Khorlin, A. F. Bochkov, L. B. Demushkina, and I. O. Zolotukhin, Zh. Obshch. Khim.,37, 1272 (1967).

    Google Scholar 

  8. N. K. Kochetkov, A. Ya. Khorlin, A. F. Bochkov, and L. G. Kretsu, Izv. Akad. Nauk SSSR, Ser. Khim., 2028 (1966).

  9. A. F. Bochkov, V. I. Snyatkova, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2684 (1967).

  10. Dictionary of Organic Compounds [Russian translation], Vol. 1, IL (1949), p. 188.

  11. A. Ya. Khorlin, A. F. Bochkov, and N. K. Kochetkov, Khim. Prirodn. Soed., 6 (1966).

  12. N. K. Kochetkov, A. F. Bochkov, and L. G. Yazlovetskii, Carbohydrate Research,5, 243 (1967).

    Google Scholar 

  13. N. K. Kochetkov, A. F. Bochkov, I. G. Yazlovetskii, and V. I. Snyatkova, Izv. Akad. Nauk SSSR, Ser. Khim., 1802 (1968).

  14. A. F. Bochkov, T. A. Sokolovskaya, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 1570 (1968).

  15. W. Korytnic and J. A. Mills, J. Chem. Soc., 636 (1959).

  16. R. U. Lemieux and J. D. T. Cipera, Canad. J. Chem.,34, 906 (1956).

    Google Scholar 

  17. M. Mazurek and A. S. Perlin, Canad. J. Chem.,43, 1918 (1965).

    Google Scholar 

  18. N. K. Kochetkov, A. Ya. Khorlin, and A. F. Bochkov, Zh. Obshch. Khim.,37, 338 (1967).

    Google Scholar 

  19. A. Ya. Khorlin, A. F. Bochkov, and N. K. Kochetkov, Izv. Akad. Nauk SSSR, Ser. Khim., 2214 (1964).

  20. G. Ya. Vidershain and E. L. Rozenfel'd, Biokhimiya,29, 735 (1964).

    Google Scholar 

  21. B. Helferich and E. Schmitz-Hillebrecht, Ber.,66, 378 (1933).

    Google Scholar 

  22. R. Robinson and J. Ch. Smith, J. Chem. Soc., 392 (1926).

  23. F. Mauthner, J. Pract. Chem.,85, 564 (1912);88, 764 (1913).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 5, pp. 1143–1147, May, 1969.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Bochkov, A.F., Dzhein, A.C. & Kochetkov, N.K. Synthesis of aryl glycosides by ortho-ester method. Russ Chem Bull 18, 1044–1047 (1969). https://doi.org/10.1007/BF00922868

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00922868

Keywords

Navigation