Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides

Andrew K. Reid, Callum J. McHugh, Graham Richie, Duncan Graham

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14 Citations (Scopus)

Abstract

The use of an acetylated benzotriazole for the selective protection of the amino groups of cytidine and 2′-deoxycytidine is reported. The use of the acetyl group is of considerable interest industrially in this role, and a single-step protection strategy advantageous in bulk production. 1-Acetyl-4-nitrobenzotriazole was found to readily acetylate the amine of cytidine preferentially over the exposed alcohol functionalities. With adaptation of the protocol, 2′-deoxycytidine was protected using the same reagent. A similar approach was attempted for the benzoylation of adenosine but was found to be unsuitable.
Original languageEnglish
Pages (from-to)4201-4203
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number25
DOIs
Publication statusPublished - 19 Jun 2006
Externally publishedYes

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