Nucleosides and Nucleotides. XII. Synthesis and Properties of 2′-Deoxy-2′-mercaptouridine and Its Derivatives

Abstract

New thiosugar nucleosides, 2′-deoxy-2′-mercaptouridine (III), its disulfide (IV), 2′-deoxy-2′-mercapto-3′,5′-di-O-acetyluridine (V), and 2′-deoxy-2′-methyl-thiouridine (VI) have been synthesized. The present synthetic method involves the use of 2′-deoxy-2′-acetylthio-3′,5′-di-O-acetyluridine (II) as the intermediate which was obtained by the reaction of 2,2′-cyclo-3′,5′-di-O-acetyluridine (I) with thioacetic acid. The proton magnetic resonance (PMR) data of these compounds suggested that the introduction of sulfur atom at 2′-position resulted in the furanose ring puckering that is extremely biased to C2′ endo-mode. 2′-Deoxy-2′,6-epithio-5,6-dihydro-arabinofuranosyluracil (VIIIb), the 2′-epimer of III in an 2′,6-epithio form, was also synthesized. © 1975, The Pharmaceutical Society of Japan. All rights reserved.