Tetrahedron letters

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

AK Reid, CJ McHugh, G Richie, D Graham

Index: Reid, Andrew K.; McHugh, Callum J.; Richie, Graham; Graham, Duncan Tetrahedron Letters, 2006 , vol. 47, # 25 p. 4201 - 4203

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Citation Number: 13

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′ ...