Related Experiment Video
Updated: Jul 14, 2026

Nucleoside Triphosphates - From Synthesis to Biochemical Characterization
Published on: April 3, 2014
Stereoselective preparation of (RP)-8-hetaryladenosine-3',5'-cyclic phosphorothioic acids
Mioara Andrei1, Vidar Bjørnstad, Geir Langli
1Lauras, Gaustadalleen 21, N-0349, 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.
Related Concept Videos
Preparation of Acid Anhydrides
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
α-Bromination of Carboxylic Acids: Hell–Volhard–Zelinski Reaction
Prochirality
Sharpless Epoxidation
Chirality at Nitrogen, Phosphorus, and Sulfur
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
