Skip to main content
Log in

Synthesis of azido derivative from 2(3)-O-tosyl-6-O-tritylcellulose and its conversion to an a minopolysacchride

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

Conclusions

  1. 1.

    (2)3-Azido-(2)3-desoxy-6-O-tritylpolysaccharide was synthesized by replacing the tosyloxy groups by azide groups in 2(3)-O-tosyl-6-O-triacetylcellulose in hexamethylphosphoric triamide medium, the reduction of which with aluminum lithium hydride gave a (2)3-amino-(2)3-desoxypolysaccharide with a degree of substitution of 0.5–0.7 in amino groups.

  2. 2.

    The tosylation of 6-O-tritylcellulose goes predominantly at C-2. When the degree of substitution of tosyloxy groups is 0.7 the degree of substitution of tosyloxy groups at C-2 is equal to 0.6, and 0.1 at C-3.

  3. 3.

    The replacement of tosyloxy groups by azide groups in the 2-O-tosyl-6-O-tritylglucose units of 2(3)-O-tosyl-6-O-tritylcellulose goes predominantly via the formation of 2,3-anhydro rings, the opening of which by the azide anion proceeds mainly via attack at C-3. The reaction proceeds to a lesser degree via the direct replacement of the tosyloxy groups by the azide anion, with an inversion of the configuration at C-2. In contrast, the insertion of azide groups into the 3-O-tosyl-6-O-tritylglucose units proceeds mainly by direct substitution.

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.

Institutional subscriptions

Similar content being viewed by others

Literature cited

  1. A. I. Usov, N. I. Nosova, S. I. Firgang, and O. P. Golova, Vysokomolekul. Soedin.,15A, 1150 (1973).

    Google Scholar 

  2. W. M. Hearon, G. D. Hiatt, and C. R. Fordyce, J. Am. Chem. Soc.,65, 2449 (1943).

    Google Scholar 

  3. J. Honeyman, J. Chem. Soc., 168 (1947).

  4. G. N. Smirnova, A. I. Polyakov, and Z. A. Rogovin, Vysokomolekul. Soedin.,7, 972 (1965).

    Google Scholar 

  5. R. D. Guthrie and D. Murphy, J. Chem. Soc., 5288 (1963).

  6. F. D. Cramer, H. Otterbach, and H. Springman, Chem. Ber.,92, 384 (1953).

    Google Scholar 

  7. J. Jary, Z. Kefurtova, and J. Kovar, Collect. Czechoslov. Chem. Commun.,34, 1452 (1969).

    Google Scholar 

  8. L. F. Wiggins, J. Chem. Soc., 18 (1947).

  9. R. L. Whistler and L. W. Doner, J. Org. Chem.,35, 3562 (1970).

    Google Scholar 

  10. U. G. Noyak and R. L. Whistler, J. Org. Chem.,34, 3819 (1969).

    Google Scholar 

  11. R. V. Lemieux and P. Chu, J. Am. Chem. Soc.,80, 4745 (1958).

    Google Scholar 

  12. S. Roseman and J. Ludowieg, J. Am. Chem. Soc.,76, 301 (1954).

    Google Scholar 

  13. A. B. Foster, M. Stacey, and S. V. Vardheim, Acta Chem. Scand.,12, 1605 (1958).

    Google Scholar 

  14. P. A. Levene and G. M. Meyers, J. Biol. Chem.,55, 221 (1923).

    Google Scholar 

  15. R. Kuhn, W. Bister, and H. Fischer, Ann. Chem.,617, 109 (1958).

    Google Scholar 

  16. H. H. Baer, J. Am. Chem. Soc.,84, 83 (1962).

    Google Scholar 

  17. B. Coxon and L. Hough, J. Chem. Soc., 1463 (1961).

  18. B. Coxon and L. Hough, J. Chem. Soc., 1643 (1961).

  19. Y. Ali and A. C. Richardson, Carbohyd. Res.,5, 441 (1967).

    Google Scholar 

  20. A. Gotshalka (editor), Glycoproteins (Russian translation], Vol. 1, Mir (1969), p. 200.

  21. S. Peat and L. F. Wiggins, J. Chem. Soc., 1810 (1938).

  22. I. Jezo, Chem. Zvesti,27, 381 (1973).

    Google Scholar 

  23. R. D. Guthrie, A. M. Prior, and S. E. Creasey, J. Chem. Soc., C 1961 (1970).

    Google Scholar 

  24. N. A. Hughes and P. R. H. Speakman, J. Chem. Soc., 2236 (1965).

  25. T. S. Gardner and C. B. Purves, J. Am. Chem. Soc.,64, 1539 (1942).

    Google Scholar 

  26. F. G. Fischer and N. J. Nebel, Z. Physik. Chem.,302, 10 (1955).

    Google Scholar 

  27. L. S. Bolotnikova, S. N. Danilov, and T. I. Samsonova, Zh. Prikl. Khim.,39, 176 (1966).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2575–2581, November, 1974.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Usov, A.I., Nosova, N.I., Firgang, S.I. et al. Synthesis of azido derivative from 2(3)-O-tosyl-6-O-tritylcellulose and its conversion to an a minopolysacchride. Russ Chem Bull 23, 2481–2487 (1974). https://doi.org/10.1007/BF00922136

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00922136

Keywords

Navigation