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Original Articles

Evidence for the Stereoelectronic Control of the Acid Hydrolysis of Adenosine Cyclic 3′,5′-Phosphoramidate Diastereoisomers

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Pages 1217-1229 | Received 15 Aug 1988, Published online: 24 Oct 2006

References

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  • Tomasz , J. , Bottka , S. and Radics , L. Nucleosides and Nucleotides submitted for publication. Recent NMR data corroborate a pyramidal arrangement of substituents around the amide nitrogen atom in 1
  • Bentrude pointed out7,8 that as a result of the transoid five-to-six-membered ring fusion, one chair and a single twist conformation are accessible for the dioxaphosphorinane ring of such compounds.
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  • Unpublished NMR data by Bentrude et al. show that the chair conformation is populated predominantly for both R-P-1 (about 90%) and for S-P-1 (about 100%) in DMSO-d6 solution.
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  • The primary products of ester bond breakings, 9(6-deoxy–α-L-talofuranosyl)adenine 5′-phosphoramidate and 9(6-deoxy-α-L-talofuranosyl)adenine 3′-phosphoramidate were converted to 10 and 11, respectively, during the acid hydrolysis, as expected on the basis of literature data.2,3,25
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