Nucleosides, Nucleotides & Nucleic Acids 2004-01-01

Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: synthesis of methoxy TEMPO substituted pyrimidine nucleoside analogs.

Kevin M Church, Liesel M Holloway, Ryan C Matley, Robert J Brower

Index: Nucleosides Nucleotides Nucleic Acids 23(11) , 1723-38, (2004)

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Abstract

Our work outlines the use of oxoammonium salts in a formal 1,2 addition process to olefins giving nucleoside analogs as products. Specifically, oxoammonium salts can be added to a solution of olefin and silylated heterocycle to give Methoxy TEMPO substituted nucleoside analogs after hydrolytic workup and chromatographic purification.