Russian Journal of Bioorganic Chemistry

, Volume 31, Issue 5, pp 460–466 | Cite as

A Synthesis of Heteroaromatic S- and N-β-Glycosides of N-Acetylglucosamine under Phase-Transfer Conditions

  • V. O. Kur'yanov
  • T. A. Chupakhina
  • A. E. Zemlyakov
  • V. Ya. Chirva
  • O. V. Shishkin
  • S. V. Shishkina
  • S. A. Kotlyar
  • G. L. Kamalov


The use of crown ethers for a phase transfer-catalyzed synthesis of heteroaromatic glycosides of N-acetylglucosamine was studied. The solid-liquid system and catalysis by 15-crown-5 were found to provide for both the 100% conversion of α-D-glucosaminyl chloride peracetate and a high reaction rate. The interaction of α-D-glucosaminyl chloride peracetate and oxadiazole and triazole mercapto derivatives capable of thiol-thione tautomerism carried out at room temperature in acetonitrile in the presence of anhydrous potassium carbonate and crown ethers was shown to lead to both S- and N-glucosides. The structures of the compounds synthesized were confirmed by X-ray analysis and 13C and 1H NMR spectroscopy.

Key words

crown ethers glycosylation heteroaromatic glycosides phase transfer catalysis X-ray analysis 







crown ether


phase transfer catalysis


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Copyright information

© MAIK "Nauka/Interperiodica" 2005

Authors and Affiliations

  • V. O. Kur'yanov
    • 1
  • T. A. Chupakhina
    • 1
  • A. E. Zemlyakov
    • 1
  • V. Ya. Chirva
    • 1
  • O. V. Shishkin
    • 2
  • S. V. Shishkina
    • 2
  • S. A. Kotlyar
    • 3
  • G. L. Kamalov
    • 3
  1. 1.Vernadsky Tauric National UniversitySimferopolUkraine
  2. 2.Institute of Scintillation Materials, Institute of Single Crystals Scientific Research CenterNational Academy of SciencesUkraine
  3. 3.Bogatsky Physicochemical InstituteNational Academy of SciencesUkraine

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