A Diastereoselective Synthesis of 5′-Substituted-Uridine Derivatives

A straightforward
strategy for the synthesis of 5′-substituted-uridine
derivatives is described. It relies on the introduction of various
substituents at C-5′ at the last step of the synthesis by regioselective
nucleophilic opening of a unique epoxide that provides access to a
small library of compounds. This epoxide results from the diastereoselective
epoxidation, performed at a multigram scale, of a uridine-derived
alkene. The configuration of the newly created 5′ asymmetric
center has been unambiguously assigned by X-ray diffraction analysis.