SYNTHETIC ROUTE TO 5-SUBSTITUTED URIDINES VIA A NEW TYPE OF DESULFURIZATIVE STANNYLATION

Article abstract of DOI:10.1016/S0040-4020(01)87642-0

Phenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidine.Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives.The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis.The whole sequence constitutes a new route to 5-substituted uridines.Application of this method to 2'-deoxyuridine is also described.