Synthesis of 5'-amino-5'-phosphonate analogues of pyrimidine nucleoside monophosphates.
The 5'-amino-5'-phosphono derivatives of cytidine, cytosine arabinoside (ara-C), and uridine have been prepared via the corresponding nucleoside aldehydes. Phosphite addition to imines derived from the nucleoside aldehydes and p-methoxybenzylamine was efficient, and use of this amine allowed cleavage of the products to the parent amino phosphonic acids. The phosphite additions proved to be diastereoselective, with the cytidine and uridine derivatives favoring the 5'S stereochemistry and the ara-C derivative favoring the 5'R isomer. The stereochemistry of one cytidine derivative was established by single-crystal diffraction analysis, and detailed comparisons of the (13)C NMR data allowed assignments of the other amino phosphonates.
Chen
Xuemei
X
Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, USA.
Wiemer
David F
DF
D002855:Chromatography, Thin Layer; D003561:Cytarabine / Q000737:chemistry; D003562:Cytidine / Q000138:chemical synthesis / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014529:Uridine / Q000138:chemical synthesis / Q000737:chemistry
D007202:Indicators and Reagents; D063065:Organophosphonates; D011741:Pyrimidine Nucleosides; D003561:Cytarabine; D003562:Cytidine; D014529:Uridine