Chemical and Pharmaceutical Bulletin · 1975 · 17 citations · 0 references
Natural SciencesChemistryNucleic Acid ChemistryOrganic ChemistrySynthetic Medicinal ChemistryNucleic Acid SynthesisNucleobase ChemistryOrganic SynthesisCyclic Nucleotide SynthesisNucleobase SynthesisNucleoside Analog SynthesisNucleoside AnalogsNucleotide Analogue Synthesis
The reaction of various nucleosides (III) with trichloromethylphosphonic acid dichloride in triethyl phosphate or m-cresol afforded nucleoside 5'-trichloromethylphosphonates (IV). The intramolecular cyclization of IV with potassium t-butoxide in dimethyl sulfoxide or N, N-dimethylformamide led to the synthesis of nucleoside 3', 5'-cyclic phosphates (I) in high yields by fission of the C-P bond of the phosphonate (IV).