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Russian Journal of Organic Chemistry

, Volume 46, Issue 6, pp 860–865 | Cite as

Structure of aldose condensation products with 2-hydroxyand 2-sulfanylbenzohydrazides

  • V. V. Alekseev
  • A. Yu. Ershov
  • B. V. Chernitsa
  • V. A. Doroshenko
  • I. V. Lagoda
  • S. I. Yakimovich
  • I. V. Zerova
  • V. V. Pakal’nis
  • V. V. Shamanin
Article

Abstract

The structure of the condensation products of 2-hydroxy- and 2-sulfanylbenzohydrazides with a series of aldoses (L-arabinose, D-ribose, L-ramnose, D-galactose, D-glucose, D-mannose) was studied by 1H and 13C NMR spectroscopy. The condensation products of monosaccharides with 2-hydroxybenzohydrazide in DMSO-d 6 solution exist as equilibrium mixtures of linear hydrazone and cyclic pyranose and furanose forms, the cyclic tautomers being represented by two stereoisomers (α- and β-anomers). The aldose condensation products with 2-sulfanylbenzohydrazide in the crystalline state have cyclic 1,3,4-benzothiadiazepine structure, while in DMSO-d 6 solution they undergo complete or partial isomerization into cyclic pyranose tautomer.

Keywords

Aldose Condensation Product Cross Polarization Magic Angle Spin Furanose Form Cyclic Tautomer 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2010

Authors and Affiliations

  • V. V. Alekseev
    • 1
  • A. Yu. Ershov
    • 2
  • B. V. Chernitsa
    • 2
  • V. A. Doroshenko
    • 2
  • I. V. Lagoda
    • 3
  • S. I. Yakimovich
    • 4
  • I. V. Zerova
    • 4
  • V. V. Pakal’nis
    • 4
  • V. V. Shamanin
    • 2
  1. 1.Military Medical AcademyMinistry of Defense of the Russian FederationSt.-PetersburgRussia
  2. 2.Institute of High-Molecular CompoundsRussian Academy of SciencesSt.-PetersburgRussia
  3. 3.Research Test Center of Medical and Biological Protection, State Research Test Institute of Military MedicineMinistry of Defense of the Russian FederationSt.-PetersburgRussia
  4. 4.St. Petersburg State UniversitySt. PetersburgRussia

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