Abstract
A simple and efficient route to N 6 -acetyl-2′,3′,5′-tri- O-acetyladenosine ( 1)was developed based on selective N-deacetylation of pentaacetylatedadenosine 2 with methanol at room temperaturein the presence of imidazole. Preparative synthesis of 1 was elaborated utilizing a crude mixtureof 2 and 1 whichis produced by reaction of adenosine with acetic anhydride in pyridineat elevated temperatures. The total yield of 1 was80-85% starting with adenosine. It was shown that 1 is a convenient substrate for selectiveN 6 -alkylations. The study revealed the same regioselectivityin base-promoted reactions of 1 with activatedalkyl halides and Mitsunobu reactions of 1 withalcohols. A series of N 6 -alkyladenosines 5A- F wereprepared. Cytokinins 6B, D, E were prepared by enzymatic transformationof parent nucleoside derivatives 5B, D, E using a combinationof nucleoside phosphorylase and alkaline phosphatase.
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