Collect. Czech. Chem. Commun. 1985, 50, 1507-1513

Phosphonylmethyl analogues of ribonucleoside 2',3'-cyclic phosphates and 2'(3')-nucleotide methyl esters: Synthesis and properties

Ivan Rosenberg and Antonín Holý

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


2'(3')-O-Phosphonylmethylribonucleosides II, III were prepared by intramolecular cyclisation of ribonucleoside 2'(3')-chloromethanephosphonates I in alkali. Treatment of the phosphonylmethyl derivatives with dicyclohexylcarbodiimide afforded cyclic six-membered esters VI, VII which are stable in acid and easily hydrolyze in alkali. Ribonucleases A, T1, T2, U2 and spleen cPDase do not split the cyclic phosphonate ester linkage of these analogues of ribonucleoside 2',3'-cyclic phosphonates.