Synthesis of 2′- and 3′-O-acyluridines

Abstract

A method for the synthesis of 2′- and 3′-O-acyluridines is described. It involves the preparation of 2′,5′- and 3′,5′-di-O-benzyluridines as key intermediates, and is exemplified by the preparation of 2′- and 3′-O-pivaloyluridine. An attempt to prepare 2′- and 3′-O-L-valyluridine led to a mixture of isomers; interconversion occurred during the final stage. The possible utility in an oligoribonucleotide synthesis of 5′-O-acetyl-2′-O-trityluridine, an intermediate in the synthesis of 3′,5′-di-O-benzyluridine, is discussed.