Abstract
8.2-Anhydro-9-β-D-arabinofuranosyladenine (I) was converted to 5'-tosyl derivative (II) in a yield of 75%. When Compound (II) was heated with sodium hydrogen sulfide in dimethylformamide (DMF) 8, 5'-S-cyclonucleoside having arabinosyl configuration (IV) was obtained in a yield of 46%. From the ditosyl derivative (III) analogously a cyclonucleoside having 3'-tosyl group (VII) was obtained. 8, 3'-Anhydro-9-β-D-xylofuranosyladenine (VIII) was converted to 5'-tosyl derivative (IX) and heated with sodium hydrogensulfide in DMF. In addition to a 8, 5-S-cyclonucleoside of xylofuranosyl configuration (X), two compounds, 8, 3'-anhydro-8-oxy-9-(5'-deoxy-5'-mercapto-β-D-xylofuranosyl) adenine disulfide (XI) and 5'-deoxy-5'-mercapto-8-oxy-9-β-D-xylofuranosyladenine (XII) was obtained. Compound (XII) was also obtained from X by the treatment with 0.01N sodium hydroxide. Thus, the OH group of xylo configuration in the sugar moiety of 8, 5'-S-cyclonucleoside was found to be able to cleave the S-hydro linkage even in a mild condition.
