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

Mioara Andrei; Vidar Bjørnstad; Geir Langli; Christian Rømming; Jo Klaveness; Kjetil Taskén; Kjell Undheim

doi:10.1039/B702403G

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

Mioara Andrei,^a Vidar Bjørnstad,^ab Geir Langli,^a Christian Rømming,^c Jo Klaveness,^b Kjetil Taskén^ad and Kjell Undheim*^ac

Author affiliations

* Corresponding authors

^a Lauras, Gaustadalleen 21, Oslo, Norway

^b School of Pharmacy, University of Oslo, Oslo, Norway

^c Department of Chemistry, University of Oslo, Oslo, Norway
E-mail: kjell.undheim@kjemi.uio.no
Fax: +47 22855507

^d The Biotechnology Centre of Oslo, University of Oslo, Oslo, Norway

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 (S_P)-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (R_P)-phosphorothioic acids.

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Article information

DOI: https://doi.org/10.1039/B702403G
Article type: Paper
Submitted: 15 Feb 2007
Accepted: 02 May 2007
First published: 29 May 2007

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Org. Biomol. Chem., 2007,5, 2070-2080

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Stereoselective preparation of (R_P)-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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Organic & Biomolecular Chemistry