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Russian Journal of General Chemistry

, Volume 89, Issue 2, pp 292–299 | Cite as

Synthesis of Mono- and Disaccharide 4-[(ω-Sulfanylalkyl)oxy]benzoylhydrazones as Potential Glycoligands for Noble Metal Nanoparticles

  • A. Yu. ErshovEmail author
  • A. A. Martynenkov
  • I. V. Lagoda
  • A. V. Yakimansky
Article
  • 6 Downloads

Abstract

A procedure has been developed for the synthesis of previously unknown aldose 4-[(ω-sulfanylalkyl) oxy]benzoylhydrazones (where alkyl is hexyl or decyl and aldoses are D-glucose, D-galactose, D-maltose, and D-lactose) that a repromising glycoligands for noble metal nanoparticles. According to the 1H and 13C NMR data, 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones derived from D-glucose, D-maltose, and D-lactose in crystal and in DMSO-d6 solution have exclusively the cyclic pyranose structure (α- and β-anomers). D-Galactose 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones in DMSO-d6 solution exist as tautomeric mixtures of cyclic pyranose and open-chain acylhydrazone structures.

Keywords

thiol-containing mono- and disaccharide acylhydrazones ring—chain tautomerism 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. Yu. Ershov
    • 1
    • 2
    Email author
  • A. A. Martynenkov
    • 1
  • I. V. Lagoda
    • 3
  • A. V. Yakimansky
    • 1
    • 4
  1. 1.Institute of Macromolecular CompoundsRussian Academy of SciencesSt. PetersburgRussia
  2. 2.St. Petersburg State Institute of TechnologySt. PetersburgRussia
  3. 3.State Research Testing Institute of Military MedicineMinistry of Defense of the Russian FederationSt. PetersburgRussia
  4. 4.St. Petersburg State UniversitySt. PetersburgRussia

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