title: Stereoselective preparation of (RP)-8-hetaryladenosine-3',5'-cyclic phosphorothioic acids.
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.
authors.affiliation: Lauras, Gaustadalleen 21, N-0349, Oslo, Norway.
authors.forename: Mioara
authors.initials: M
authors.lastname: Andrei
authors.forename: Vidar
authors.initials: V
authors.lastname: Bjørnstad
authors.forename: Geir
authors.initials: G
authors.lastname: Langli
authors.forename: Christian
authors.initials: C
authors.lastname: Rømming
authors.forename: Jo
authors.initials: J
authors.lastname: Klaveness
authors.forename: Kjetil
authors.initials: K
authors.lastname: Taskén
authors.forename: Kjell
authors.initials: K
authors.lastname: Undheim
mesh_terms: D000241:Adenosine / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D008953:Models, Anatomic; D015394:Molecular Structure; D010756:Phosphoric Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D010756:Phosphoric Acids; C030242:phosphoric acid; D000241:Adenosine