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

Reid, Andrew K. and McHugh, C.J. and Richie, Graham and Graham, D. (2006) Electron-deficient benzotriazoles for the selective N-acetylation of nucleosides. Tetrahedron Letters, 47 (25). pp. 4201-4203. ISSN 0040-4039

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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.