Skip to main content
SpringerLink
Log in

Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

Glycosylation of 4-(4-hydroxyphenyl)-1,2,3-thia(selena)diazoles with 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-glucopyranose, 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose, and 1-α-bromo-2,3,5-tri-O-acetyl-D-xylopyranose under the conditions of interphase catalysis has afforded the corresponding acetylated glycosides. An alternative pathway of selenadiasole glycosides synthesis from semicarbazones of 1-β-O-(4-acetylphenyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose, -2,3,4,6-tetra-O-acetyl-D-galactopyranose, and -2,3,5-tri-O-acetyl-D-xylopyranose via oxidation with selenium dioxide has been elaborated.

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. Zuo, X., Mi, N., Fan, Zh., Zheng, Q., Zhung, H., Wang, H., and Yang, Z., J. Agric. Food Chem., 2010, vol. 58, p. 2755. doi https://doi.org/10.1021/jf902863z

    Article  CAS  PubMed  Google Scholar 

  2. Jadhav, A.A., Dhanwe, V.P., Joshi, P.G., and Khanna, P.K., Cogent Chem., 2016, no. 2, p. 1144670. doi https://doi.org/10.1080/23312009.2016.11444670

  3. Way2Drug.com©2011-2018.Version 2.0.

  4. Pavlov, A.E., Sokolov, V.M., and Zakharov, V.I., Russ. J. Gen. Chem., 2001, vol. 71, no. 11, p. 1814. doi https://doi.org/10.1023/A:101397121

    Article  Google Scholar 

  5. Dess, D., Kleine, H.P., Weinberg, D.V, Kaufman, R.J., and Sidhu, R.S., Synthesis, 1981, no. 11, p. 883. doi https://doi.org/10.1055/s-1981-29361

  6. Caplin, A., J. Chem. Soc. Perkin Trans. 1, 1974, p. 30. doi https://doi.org/10.1039/P19740000030

  7. Petrov, M.L., Lyapunova, A.G., and Androsov, D.A., Russ. J. Org. Chem., 2012, vol. 48, no. 1, p. 147. doi https://doi.org/10.1134/s1070428012010265

    Article  CAS  Google Scholar 

Download references

Funding

This study was carried out in the scope of the basic part of state project of Ministry of Education and Science of the Russian Federation, project no 4.5554.2017/8.9, using the equipment of the Resource Centers of St. Petersburg State University “Methods of analysis of composition of substance” and “X-ray diffraction methods of investigation”

Author information

Authors and Affiliations

  1. St. Petersburg State Institute of Technology (Technical University), Moskovskii pr. 26, St. Petersburg, 190013, Russia

    L. M. Pevzner & M. L. Petrov

  2. St. Petersburg State University, St. Petersburg, Russia

    E. B. Erkhitueva & A. V. Stepakov

  3. Institute of Experimental Medicine, St. Petersburg, Russia

    V. A. Polukeev

Authors
  1. L. M. Pevzner
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. L. Petrov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. B. Erkhitueva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. A. Polukeev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Stepakov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Pevzner.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 7, pp. 1038–1046.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pevzner, L.M., Petrov, M.L., Erkhitueva, E.B. et al. Synthesis of Glycosides with 4-(4-Hydroxyphenyl)-1,2,3-thia- and -selenadiazole Aglycones. Russ J Gen Chem 89, 1398–1405 (2019). https://doi.org/10.1134/S1070363219070089

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363219070089

Keywords

Search

Navigation