Synthesis and utility of 2-halo-O(6)-(benzotriazol-1-yl)-functionalized purine nucleosides

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Abstract

An efficient synthesis of 2-halo-O(6)-(benzotriazol-1-yl)-substituted purine nucleosides has been accomplished via (benzotriazol-1-yloxy)tris(dimethylamino) phosphonium hexafluorophosphate (BOP)-mediated coupling and subsequent halogenation via diazotization of the 2-amino group of various protected guanosines and directly from guanosine itself. These products are amenable to substitution and coupling reactions in the 2- and 6-positions and, accordingly, provide efficient access to highly functionalized purine nucleosides.
Original languageEnglish
Pages (from-to)1092 - 1098
Number of pages7
JournalEuropean Journal of Organic Chemistry
Volume2011
Issue number6
DOIs
Publication statusPublished - 2011

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