Synthesis of benzyl and benzyloxycarbonyl base-blocked 2'-deoxyribonucleosides

BE Watkins, H Rapoport

Index: Watkins, Bruce E.; Rapoport, Henry Journal of Organic Chemistry, 1982 , vol. 47, # 23 p. 4471 - 4477

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Citation Number: 65

Abstract

Acylimidazoles have been alkylated with trialkyloxonium tetrafluoroborates to form acylimidazolium salts. These salts, particularly (benzyloxycarbony1) 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 (4b), on treatment with phenyl ...