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Chemistry of Heterocyclic Compounds

, Volume 24, Issue 2, pp 186–191 | Cite as

Acyclic analogs of nucleosides. Synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases

  • S. G. Zavgorodnii
  • E. V. Efimtseva
  • S. N. Mikhailov
  • T. L. Tsilevich
  • A. É. Yavorskii
  • V. L. Florent'ev
Article

Abstract

A convenient method for the synthesis of 1,5-dihydroxy-3-oxa-2-pentyl derivatives of nucleic bases, which consists in the condensation of trimethylsilyl derivatives of nucleic bases with 1,2,5-triacetoxy-3-oxapentane in the presence of SnCl4, is proposed. Optically active derivatives — (R)- and (S)-1-(1,5-dihydroxy-3-oxa-2-pentyl)uracil, respectively — were obtained by periodate oxidation of α-L- and α-D-arabinopyranosyluracil.

Keywords

Oxidation Organic Chemistry Nucleoside Uracil Trimethylsilyl 
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

© Plenum Publishing Corporation 1988

Authors and Affiliations

  • S. G. Zavgorodnii
    • 1
    • 2
    • 3
  • E. V. Efimtseva
    • 1
    • 2
    • 3
  • S. N. Mikhailov
    • 1
    • 2
    • 3
  • T. L. Tsilevich
    • 1
    • 2
    • 3
  • A. É. Yavorskii
    • 1
    • 2
    • 3
  • V. L. Florent'ev
    • 1
    • 2
    • 3
  1. 1.Institute of Molecular BiologyAcademy of Sciences of the USSRMoscow
  2. 2.Branch for the Development of Ready-Made MedicinalsScientific-Research Institute for the Biological Testing of Chemical CompoundsMoscow
  3. 3.T. G. Shevchenko Kiev State UniversityKiev

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