Advertisement

Russian Journal of General Chemistry

, Volume 89, Issue 7, pp 1398–1405 | Cite as

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

  • L. M. PevznerEmail author
  • M. L. Petrov
  • E. B. Erkhitueva
  • V. A. Polukeev
  • A. V. Stepakov
Article
  • 5 Downloads

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.

Keywords

glycosylation Könnigs-Knorr reaction interphase catalysis 1,2,3-thiadiazoles semicarbazides 1,2,3-selenadiazoles 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Notes

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”

References

  1. 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 CrossRefGoogle Scholar
  2. 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. 3.
    Way2Drug.com©2011-2018.Version 2.0.Google Scholar
  4. 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 CrossRefGoogle Scholar
  5. 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. 6.
    Caplin, A., J. Chem. Soc. Perkin Trans. 1, 1974, p. 30. doi  https://doi.org/10.1039/P19740000030
  7. 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 CrossRefGoogle Scholar

Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • L. M. Pevzner
    • 1
    Email author
  • M. L. Petrov
    • 1
  • E. B. Erkhitueva
    • 2
  • V. A. Polukeev
    • 3
  • A. V. Stepakov
    • 2
  1. 1.St. Petersburg State Institute of Technology (Technical University)St. PetersburgRussia
  2. 2.St. Petersburg State UniversitySt. PetersburgRussia
  3. 3.Institute of Experimental MedicineSt. PetersburgRussia

Personalised recommendations