title: Nucleoside 3',5'-cyclic H-phosphonates, new useful precursors for the synthesis of nucleoside 3',5'-cyclic phosphates and their analogues.
abstract: Nucleoside H-phosphonates activated with a condensing agent spontaneously formed nucleoside 3',5'-cyclic H-phosphonates. The cyclization was stereoselective and produced one of the P-diastereomers in preponderance (de ca. 80%). Nucleoside 3',5'-cyclic H-phosphonates were stereochemically unstable and underwent epimerization affording the thermodynamically more stable diastereomer as a major product (de ca. 80%). They were susceptible to hydrolysis, transesterification, and oxidation and by changing oxidation protocols nucleoside 3',5'-cyclic phosphate analogues, e.g. phosphodiesters, phosphorothioate diesters, and phosphotriesters, were obtained.
authors.affiliation: Institute of Bioorganic Chemistry, Polish Academy of Sciences, Noskowskiego 12/14, 61-704 Poznań, Poland.
authors.forename: Malgorzata
authors.initials: M
authors.lastname: Rozniewska
authors.forename: Jacek
authors.initials: J
authors.lastname: Stawinski
authors.forename: Adam
authors.initials: A
authors.lastname: Kraszewski
mesh_terms: D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates; D009946:Organothiophosphorus Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction
chemical_list: D009705:Nucleosides; D009711:Nucleotides; D063065:Organophosphonates; D009946:Organothiophosphorus Compounds