DIASTEREOSELECTIVE SYNTHESIS OF SOME CARBOCYCLIC 2'-OXA-3'-AZA-NUCLEOSIDES

Authors

  • E. Hýrošová Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237 Bratislava
  • L. Fišera Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237 Bratislava
  • R. M.-A. Jame Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237 Bratislava
  • N. Prónayová Institute of Analytical Chemistry, Slovak University of Technology, 81237 Bratislava
  • M. Medvecký Institute of Organic Chemistry, Catalysis and Petrochemistry, Slovak University of Technology, 81237 Bratislava
  • M. Koóš Institute of Chemistry, Slovak Academy of Sciences, 84538 Bratislava

DOI:

https://doi.org/10.1007/7695

Keywords:

chiral, dipolar cycloadditions, isoxazolidines, modified nucleosides, nitrones

Abstract

Two strategies for the synthesis of isoxazolidinyl nucleosides as potential antiviral agents are reported: one-step approach based on  1,3-dipolar cycloaddition of D-lyxosyl nitrone  with N,N-dibenzyl-9-vinyl adenine and two-step methodology based on the Vorbrüggen nucleosidation of the 5-acetoxyisoxazolidine.  The  chiral D-lyxosyl nitrone undergoes regioselective 1,3-dipolar cycloadditions with  N,N-dibenzyl-9-vinyl adenine and vinyl  acetate giving 5-substituted isoxazolidines  as a mixture of four diastereoisomers in good yields. The condensation of 5-acetoxyisoxazolidine  with silylated uracil, thymine, and N-acetylcytosine proceeded with moderate to  good stereoselectivity under the formation of the expected isoxazolidinyl β-and α-nucleosides.

How to Cite
Hýrošová, E.; Fišera, L.; Jame, R. M.-A.; Prónayová, N.; Medvecký, M.; Koóš, M.  Chem. Heterocycl. Compd. 2007, 43, 10. [Khim. Geterotsikl. Soedin. 2007, 14.]

For this article in the English edition see DOI 10.1007/s10593-007-0002-4

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Published

2023-04-05

Issue

No. 1 (2007)

Section

Original Papers