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

✍ Scribed by Ugo Chiacchio; Antonino Corsaro; Venerando Pistarà; Antonio Rescifina; Daniela Iannazzo; Anna Piperno; Giovanni Romeo; Roberto Romeo; Giovanni Grassi

Publisher
John Wiley and Sons
Year
2002
Tongue
English
Weight
287 KB
Volume
2002
Category
Article
ISSN
1434-193X

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✦ Synopsis

Anomeric αand 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 [a

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