Synthesis of Carbocyclic Pyrimidine Nucleosides Using the Mitsunobu Reaction - Part I: Influence of the Alcohol on N1- versus O²-Alkylation

Abstract

The Mitsunobu reaction is an important tool in carbo­cyclic nucleoside chemistry for the direct coupling of alcohols with heterocyclic bases under mild conditions. Here, we report on the influence of the alcohol on the N1- vs. O²-alkylation of N3-benzoyl­thymine under Mitsunobu conditions. Moreover, a method for predicting the product ratio of the alkylation reaction will be introduced.

Key words

Mitsunobu reaction - carbocyclic nucleosides - regio­selectivity - antiviral agents - medicinal chemistry

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  Ludek, O. R.; Balzarini, J.; Meier, C. Eur. J. Org. Chem. 2005, submitted

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Ludek, O. R.; Balzarini, J.; Krämer, T.; Meier, C. Synthesis 2005, submitted