Improved Synthesis of Adenosine Cyclic 3′, 5′-Phosphoramidates via Anhydrides. Preparation of Adenosine Cylic 3′, 5′-(Rp) - and (p)-N-Methylphosphoramidate
- 1 June 1988
- journal article
- research article
- Published by Taylor & Francis in Nucleosides, Nucleotides and Nucleic Acids
- Vol. 7 (3) , 307-319
- https://doi.org/10.1080/07328318808068712
Abstract
The two-step method for the preparation of adenosine cyclic 3′,5′-phosphoramidate diastereoisomers, which involves the activation of adenosine cyclic 3′,5′-monophosphate (1) with an acid chloride and in situ aminolysis of the anhydride intermediate (Bentrude, W.G.; Tomsaz, J. Synthesis 1984, 27; Bottka, S.; Tomasz, J. Tetrahedron Lett. 1985, 24, 2909), has been improved. The best yields were attained when 1 was reacted with 4.4 molar equivalents of phosphorus oxychloride in trimethyl phosphate at O°C for 3 h, and the solution of phosphorus oxychloride in trimethyl phosphate was pretreated with 0.5 molar equivalent of water at room temperature for 20 min. R p and S p diastereoisomers of adenosine cyclic 3′,5′-N-methyphosphoramidate and N,N-dimethylphosphoramidate have been synthesized under these experimental conditions.This publication has 11 references indexed in Scilit:
- A31P NMR Study of the Reaction of Adenosine 3′ 5′-Cyclic Monophosphate with 2, 4, 6-Triisopropylbenzenesulfonyl ChlorideNucleosides, Nucleotides and Nucleic Acids, 1987
- The question of chair-twist equilibria for the phosphate rings of nucleoside cyclic 3',5'-monophosphates. Proton NMR and x-ray crystallographic study of the diastereomers of thymidine phenyl cyclic 3',5'-monophosphateJournal of the American Chemical Society, 1987
- Adenosine cyclic 3′,5′-(RP)- and (SP)-phosphoramidates, the first representatives of nucleoside cyclic 3′,5′-phosphoramidates derived from ammoniaTetrahedron Letters, 1985
- A highly efficient one-flask method for the preparation of the individual diastereoisomers of ribonucleoside 3',5'-cyclic N-substituted phosphoramidates via the direct Appel reaction. X-ray structure of trans-5-isopropyl-2'-deoxyuridine 3',5'-cyclic N-benzylphosphoramidateThe Journal of Organic Chemistry, 1985
- Inhibitory action of certain cyclophosphate derivatives of cAMP on cAMP‐dependent protein kinasesEuropean Journal of Biochemistry, 1984
- Conformational studies of phosphorus-containing ring systems of pharmacological and biochemical importance-derivatives of cyclophosphamide and cyclic nucleotidesPhosphorus and Sulfur and the Related Elements, 1983
- Interaction of cAMP Derivatives with the ‘Stable’ CAMP‐Binding Site in the CAMP‐Dependent Protein Kinase Type IEuropean Journal of Biochemistry, 1982
- 31P-15N spin-spin coupling as a probe for the assignment of absolute configuration in RP- and SP-thymidine cyclic 3′,5′-phosphordimethylamidatesTetrahedron Letters, 1980
- Conformations of saturated cyclic phosphorus heterocycles. II. 5-tert-Butyl-2-amino-1,3,2-dioxaphosphorinanes. Apparent effects of phosphorus-nitrogen vicinal interactions on the conformational energy of amino groups on trivalent phosphorus and the influence of lone pair orientation on 3FHeqPJournal of the American Chemical Society, 1973
- Stereochemistry of organophosphorus cyclic compounds—IITetrahedron, 1973