Microwave-assisted rapid and regioselective synthesis of N-(alkoxycarbonylmethyl) nucleobases in water

Abstract

Foi desenvolvido um método fácil e ambientalmente benigno para a preparação de nucleobases N- (etioxicarbonilmetil) e N-(iso-propoxicarbonilmetil), importantes na construção de blocos para Ácidos Nucleicos Peptídicos (ANP). Todas as nucleobases são regiosseletivamente alquiladas e os produtos desejados são obtidos com rendimentos moderados a altos, sob irradiação de microondas por 8 minutos em água como solvente e na presença de Et 3 N como base A facile and eco-friendly approach has been developed for the preparation of N-(ethyoxycarbonylmethyl) nucleobases and N-(iso-propoxycarbonylmethyl) nucleobases, which are important building blocks for Peptide Nucleic Acids (PNA). All the nucleobases are regioselectively alkylated and the desired products are obtained in moderate to high yields under microwave irradiation for 8 min in water as the solvent and in the presence of Et 3 N as the base.

Simple method for fast deprotection of nucleosides by triethylamine-catalyzed methanolysis of acetates in aqueous medium

“…[1][2][3][4] Consequently, improved and abbreviated synthesis of modified nucleosides from readily available precursors is of considerable interest. [5][6][7][8][9] However, nucleosides are challenging synthetic substrates as they contain several functionalized groups that must be chemically differentiated for successful transformations. Therefore, multi-step synthesis frequently requires the introduction of protective groups and their subsequent removal.…”