Abstract:

Three natural deoxynucleosides were synthesized with a high stereoselectivity and good or excellent yield. In the preparation of 2′-deoxy-β-D-adenosine, glycosidations between 1-chloro-2-deoxy-3,5-di-O-(p-chlorobenzyl)-α-Derythro-pentofuranose and silylated adenine as well as adenine sodium salt were systematically studied. A simple synthesis route to prepare 2′-deoxy-β-D-adenosine without chromatography was developed, making 2deoxy-β-D-adenosine readily accessible in an industrial scale. High efficient synthesis of 2′-deoxy-β-D-cytidine and 2′-deoxy-β-D-thymidine were also achieved without chromatography by glycosidations between 1-chloro-2-deoxy-3,5-di-O-(p-chlorobenzyl)-α-D-erythro-pentofuranose and silylated bases via the similar procedure.

Key words: Nucleoside; Synthesis; Stereoselectivity