Stereoselective preparation of (RP)-8-hetaryladenosine-3',5'-cyclic phosphorothioic acids.
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.
Andrei
Mioara
M
Lauras, Gaustadalleen 21, N-0349, Oslo, Norway.
Bjørnstad
Vidar
V
Langli
Geir
G
Rømming
Christian
C
Klaveness
Jo
J
Taskén
Kjetil
K
Undheim
Kjell
K
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
D010756:Phosphoric Acids; C030242:phosphoric acid; D000241:Adenosine