Journal of the Brazilian Chemical Society
Print version ISSN 0103-5053
MEIER, Lidiane; MONTEIRO, Gustavo C.; BALDISSERA, Rodrigo A. M. and SA, Marcus Mandolesi. Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium. J. Braz. Chem. Soc. [online]. 2010, vol.21, n.5, pp. 859-866. ISSN 0103-5053. http://dx.doi.org/10.1590/S0103-50532010000500013.
A straightforward methodology for deacetylation of protected ribonucleosides was developed based on triethylamine-catalyzed solvolysis in aqueous methanol. Reactions are completed in a few minutes under microwave irradiation and the free nucleosides are obtained in high yield after simple evaporation of volatiles. Other important features include the involvement of readily available reagents and the compatibility with diverse functional groups, which make this process very attractive for broad application.
Keywords : nucleosides; triethylamine-catalyzed transesterification; microwave-assisted synthesis; deacetylation.