Abstract

Acylimidazoles have been alkylated with trialkyloxonium tetrafluoroborates to form acylimidazolium salts. These salts, particularly (benzyloxycarbonly)imidazolium salts, are shown to be effective agents for the direct, mono-N-protection of deoxynucleosides as their acyl derivatives. These acyl nucleosides are also available via thiocarbamate intermediates. Thus 3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine, on treatment with phenyl chlorothioformate, gave the 6-thiophenyl-substituted purine (1). The thiophenyl group of (1) can be replaced by hydrogen, amino, and alkoxy groups to give a variety of substituted purine deoxyribonucleosides.

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