Nucleic Acid Component Analogues: Synthesis of 2′-Deoxynucleosides from 5-Substituted-4- Hydroxy-6(1H)-Pyrimidinones

Abstract Condensation of the silylated pyrimidines 5a–c with methyl 2-deoxy-3,5-di-O-toluoyl-D-pentofuranoside 6, using trimethylsilyltriflate as catalyst gave anomeric mixtures of 2′-deoxynucleosides 7a–c, the pure α- and β-anomers were separated and deprotected with sodium methoxide in methanol to give 1-(2′-deoxy-α-D- pentafuranosyl)-4-hydroxy-5-substituted-6(1H)-pyrimidinones 10a,b and 13a and their corresponding β-anomers 11a,b and 13b.