Anomeric alpha- and beta-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 thermodynamiccontrol; under thermodynamic control conditions only beta-nucleosides are obtained for pyrimidine derivatives and alpha-nucleosides for purine derivatives.

Diastereoselective synthesis of N,O-psiconucleosides, a new class of modified nucleosides

IANNAZZO, Daniela;PIPERNO, Anna;ROMEO, Giovanni;ROMEO, Roberto;GRASSI, Giovanni
2002-01-01

Abstract

Anomeric alpha- and beta-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 thermodynamiccontrol; under thermodynamic control conditions only beta-nucleosides are obtained for pyrimidine derivatives and alpha-nucleosides for purine derivatives.
2002
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11570/1596115
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