RESUMEN

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.

Asunto(s)

Adenosina/química , Ácidos Fosfóricos/síntesis química , Cristalografía por Rayos X , Ciclización , Modelos Anatómicos , Estructura Molecular , Ácidos Fosfóricos/química , Estereoisomerismo