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


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.


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


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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”


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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

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