著者

今沢 正興 上田 亨 浮田 忠之進

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.23, no.3, pp.604-610, 1975-03-25 (Released:2008-03-31)

被引用文献数

19 30

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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 sulfuratom 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.