872025-83-7Relevant academic research and scientific papers
PROCESS FOR THE PREPARATION OF AN (RP)-8-SUBSTITUTED CAMPS
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Page/Page column 14-15, (2008/06/13)
This invention relates to a process for the preparation of an (Rp)-8-substituted adenosine-3',5'-cyclic phosphorothioic acid, or a salt or ester thereof, which comprises P-amidating 8-bromoadenosine-3',5'-cyclic phosphoric acid, and reacting the P-amidate with a base and with carbon disulphide to yield (Rp)-8-bromoadenosine-3',5'-cyclic phosphorothioic acid or a salt or ester thereof.
Stereoselective preparation of (RP)-8-hetaryladenosine-3′, 5′-cyclic phosphorothioic acids
Andrei, Mioara,Bjornstad, Vidar,Langli, Geir,Romming, Christian,Klaveness, Jo,Tasken, Kjetil,Undheim, Kjell
, p. 2070 - 2080 (2008/03/12)
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 (SP)-configuration. Carbon disulfide effected thiylation under strongly basic conditions stereospecifically provided the (RP)-phosphorothioic acids. The Royal Society of Chemistry.
PURINE NUCLEOTIDE DERIVATIVES
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Page/Page column 14; 87-88, (2010/02/15)
This invention provides novel 8-carbyl substituted cAMPS and a novel procedures for the preparation of 8-Br-cAMP, a key starting material.
