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Issue 13, 2007
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Stereoselective preparation of (RP)-8-hetaryladenosine-3′,5′-cyclic phosphorothioic acids

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Abstract

Cyclic adenosine monophosphate (cAMP) has been converted into its 8-bromo derivative and 2′O-TBDMS protected before activation of the phosphoric acid moiety with a reagent generated in situ from oxalyl chloride and DMF. Further reactions with primary amines furnished corresponding phosphoramidates with high stereoselectivity at the phosphorus atom. Cross-coupling reactions with the 8-bromopurine yielded 8-hetaryl derivatives. X-Ray analyses showed the amidates to possess the (SP)-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (RP)-phosphorothioic acids.

Graphical abstract: Stereoselective preparation of (RP)-8-hetaryladenosine-3′,5′-cyclic phosphorothioic acids

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Publication details

The article was received on 15 Feb 2007, accepted on 02 May 2007 and first published on 29 May 2007


Article type: Paper
DOI: 10.1039/B702403G
Org. Biomol. Chem., 2007,5, 2070-2080

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    Stereoselective preparation of (RP)-8-hetaryladenosine-3′,5′-cyclic phosphorothioic acids

    M. Andrei, V. Bjørnstad, G. Langli, C. Rømming, J. Klaveness, K. Taskén and K. Undheim, Org. Biomol. Chem., 2007, 5, 2070
    DOI: 10.1039/B702403G

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