New approach to preparation of N-acylphosphoramido(thio)(seleno)ates |
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Authors: | Janina Baraniak Renata Kaczmarek Ewa Wasilewska Dariusz Korczyński Wojciech J. Stec |
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Affiliation: | Department of Bioorganic Chemistry, Center of Molecular and Macromolecular Studies, Polish Academy of Sciences, Sienkiewicza 112, 90-363 ?ód?, Poland |
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Abstract: | N-[2-(X)-1,3,2-Oxathiaphospholane] derivatives (X = S, Se, O) of carboxamides were prepared and their DBU-assisted reaction with alcohols led to the corresponding O-alkyl-N-acylphosphoramido(thio)(seleno)ates. Their structures were confirmed by MS analysis and 1H and 31P NMR spectroscopy. Independently N-acylphosphoramidoselenoates were converted to N-acylphosphoramidates by treatment with tert-butylperoxytrimethylsilane. The oxathiaphospholane approach was also applied to the synthesis of derivatives having N-prolylphosphoramido(thio)(seleno)ate linkages on the 5′-OH group of AMP. |
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Keywords: | Carboxamides N-[2-Oxo(seleno)(thiono)-1,3,2-oxathiaphospholanyl]carboxamides O-Alkyl-N-acylphosphoramido(thio)(seleno)ates tert-Butylperoxy-trimethylsilane Prolylamido-AMP(S) Oxathiaphospholane chemistry |
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