Stereoselective β-N-glycosylation of 2,3-dideoxyribofuranose derivatives controlled by a methylenephosphonothioate functional group at the 3-position

Article abstract of DOI:10.1016/S0040-4039(98)01335-5

N-glycolylation of 3-(diethoxyphosphorothioyl)methyl-5-O-benzoyl-l-O- ethyl-2,3-dideoxyriboses 9b and 10b with silylated thymine in the presence of TiCl₄ proceeded highly diastereoselectively (92% de) to give the corresponding β-nucleotide analogues in good yield. A remarkable neighboring group participation of the methylenephosphonothioate functionality was observed in the course of the β-N-glycosylation.