Facile access to 2′- O-acyl prodrugs of 1- (β- d-arabinofuranosyl)-5( E)-(2-bromovinyl)uracil (BVAraU) via regioselective esterase-catalyzed hydrolysis of 2′ 3′, 5′-triesters 1

Abstract

Treatment of 1-(2,3,5-tri- O-acetyl-β- d-arabinofuranosyl) -5-[2-(trimethylsilyl)-vinyl]uracil ( 3) with pyridinium bromide perbromide and deacetylation gave BVAraU ( 2). Pig liver esterase (EC 3.1.1.1) catalysed the regioselective hydrolysis of 1-(2,3,5-tri- O-acyl-β- d-arabinofuranosyl)uracil derivatives to their 2′- O-acyl monoesters.