Stereoselective preparation of (RP)-8-hetaryladenosine-3',5'-cyclic phosphorothioic acids |
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Authors: | Andrei Mioara Bjørnstad Vidar Langli Geir Rømming Christian Klaveness Jo Taskén Kjetil Undheim Kjell |
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Institution: | Lauras, Gaustadalleen 21, N-0349, Oslo, Norway. |
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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 (S(P))-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (R(P))-phosphorothioic acids. |
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