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Convergent syntheses and cytostatic properties of 2-chloro-2′-deoxy-2′-fluoroadenosine and its N-isomer |
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| Authors: | Galina V Zaitseva Grigorii G Sivets Zygmunt Kazimierczuk Juhani A Vilpo Igor A Mikhailopulo |
| Institution: | a Institute of Bioorganic Chemistry, Byelorussian Academy of Sciences, 220141 Minsk, Zhodinskaya 5, Byelorussia, USSR b Department of Biophysics, Institute of Experimental Physics, University of Warsaw, Zwirki i Wigury 93, 02-089, Warsaw, Poland c Tampere University Hospital, Department of Clinical Chemistry, P.O. Box 2000, SF-33521, Tampere, Finland |
| Abstract: | Glycosylation of trimethylsilylated 2,6-dichloropurine 2 with acetate 1 in anhydrous MeCN was investigated. In the presence of SnCl4, the reaction was regio- and stereoselective affording N7-β-glycoside 3 (86%). The use of TMS-Tfl instead of SnCl4 afforded a ≈ 9:1 mixture of the N9-β- and - -glycosides 5 and 6 (90%, combined). The title nucleosides were tested for their cytotoxicity. |
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