Anomeric α- and β-N,O-psiconucleosides were prepared by 1,3-dipolar cycloaddition of C-ethoxycarbonyl N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by Vorbrüggen nucleosidation. The synthetic scheme has been applied to all purine and pyrimidine nucleobases. Nucleosidation can proceed under kinetic and under thermodynamic control; under thermodynamic control conditions only β-nucleosides are obtained for pyrimidine derivatives and α-nucleosides for purine derivatives

Diastereoselective Synthesis of N,O-Psiconucleosides, a New Class of Modified Nucleosides

CHIACCHIO, Ugo;PISTARA', Venerando;RESCIFINA, Antonio;
2002-01-01

Abstract

Anomeric α- and β-N,O-psiconucleosides were prepared by 1,3-dipolar cycloaddition of C-ethoxycarbonyl N-methyl nitrone with ethyl 2-acetyloxyacrylate, followed by Vorbrüggen nucleosidation. The synthetic scheme has been applied to all purine and pyrimidine nucleobases. Nucleosidation can proceed under kinetic and under thermodynamic control; under thermodynamic control conditions only β-nucleosides are obtained for pyrimidine derivatives and α-nucleosides for purine derivatives
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/20.500.11769/37366
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 38
  • ???jsp.display-item.citation.isi??? 35
social impact