1.
J Org Chem
; 79(16): 7758-65, 2014 Aug 15.
Article
in English
| MEDLINE
| ID: mdl-25036849
ABSTRACT
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.