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Diastereoselective Synthesis of N,O ‐Psiconucleosides, a New Class of Modified Nucleosides
Author(s) -
Chiacchio Ugo,
Corsaro Antonino,
Pistarà Venerando,
Rescifina Antonio,
Iannazzo Daniela,
Piperno Anna,
Romeo Giovanni,
Romeo Roberto,
Grassi Giovanni
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200204)2002:7<1206::aid-ejoc1206>3.0.co;2-0
Subject(s) - chemistry , pyrimidine , nitrone , anomer , cycloaddition , nucleobase , purine , stereochemistry , bicyclic molecule , kinetic control , organic chemistry , combinatorial chemistry , dna , enzyme , catalysis , biochemistry
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. (© Wiley‐VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)