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- W2087533061 abstract "2′-Desoxytubercidin (1), ein Isoster des 2′-Desoxyadenosins (2), wurde durch Phasentransfer-glycosylierung des Chromophors 3a mit der toluoylgeschützten Halogenose 6 unter Umgehung natürlicher Vorstufen dargestellt. Bei der Glycosylierung entsteht nur das β-Anomer. Nach alkalischer Hydrolyse der Schutzgruppen von 5a wird 2′-Desoxy-2-(methylthio)tubercidin (5b) erhalten, das nach Entschwefeln mit Raney-Nickel die Titelverbindung 1 ergibt. Die Glycosylierungsposition N-7 konnte mit Hilfe der 13C, 1H-NMR-Fernkopplung zwischen C-6 und 1′-H festgelegt werden. 2′-Deoxytubercidin – Synthesis of a 2-Deoxyadenosine Isoster by Phase-Transfer Glycosylation 2′-Deoxytubercidin (1), an isoster of 2′-deoxyadenosine (2), has been synthesized omitting naturally occurring synthons via phase-transfer glycosylation of the chromophore 3a with the toluoyl-protected halogenose 6. The glycosylation reaction produces the β-anomer exclusively. Alkaline hydrolysis of the protecting groups of 5a yields 2′-deoxy-2-(methylthio)tubercidin (5b). Desulfurization with Raney nickel catalyst gives 2′-deoxytubercidin (1). The position of glycosylation has been determined by 13C NMR spectroscopy using the long-range coupling constant between C-6 and 1′-H and was found to be N-7." @default.
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- W2087533061 date "1983-05-16" @default.
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- W2087533061 title "2′-Desoxytubercidin – Synthese eines 2′-Desoxyadenosin-Isosteren durch Phasentrasferglycosylierung" @default.
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- W2087533061 doi "https://doi.org/10.1002/jlac.198319830513" @default.
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