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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 …

KA Nelson, WG Bentrude, WN Setzer…

文献索引:Nelson, Keith A.; Bentrude, Wesley G.; Setzer, William N.; Hutchinson, John P. Journal of the American Chemical Society, 1987 ,  vol. 109,  # 13  p. 4058 - 4064

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被引用次数: 51

摘要

Abstract: The diastereomeric cis and trans forms of thymidine phenyl cyclic 3', 5'- monophosphate triesters 5 were synthesized starting with the corresponding cyclic N, N- dimethyl phosphoramide. X-ray crystallography unequivocally identified the trans diastereomer (PhO and I-thyminyl, trans).'H NMR analysis shows the phosphate ring of cis-5 to be in the chair conformation with the PhO axial. trans-5 features a chair s twist ...