Synthesis and the Crystal Structure of 4-(2-Deoxy-β-D-erythro-pentofuranosyl)-6-methyl-1,2,4-triazin-3(4H)-one 1-Oxide, a Structural Analogue of Thymidine

Article abstract of DOI:10.1021/jo00345a002

Condensation of pyruvaldehyde dimethyl acetal with thiosemicarbazide, followed by methylation and cyclization, gave 3-(methylthio)-6-methyl-1,2,4-triazine, which was converted to 6-methyl-1,2,4-triazin-3(4H)-one 1-oxide by treatment with sodium methoxide and by selective oxidation and hydrolysis.Following silylation, this intermediate was condensed with blocked 2-deoxyribofuranosyl chloride, providing the anomeric nucleoside mixture, which was separated and deblocked to furnish the title compound.X-ray analysis of this nucleoside was carried out to confirm its structure and to study its conformation.