title: Synthesis of nucleoside phosphorothio-, phosphorodithio- and phosphoroselenoate diesters via oxidative esterification of the corresponding H-phosphonate analogues.
abstract: It was found that nucleoside H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters in the presence of iodine underwent rapid oxidative esterification with various hydroxylic components to produce in "one pot" reactions the corresponding nucleoside phosphorothioate, nucleoside phosphorodithioate and nucleoside phosphoroselenoate diesters in good yields. The transformation represents a novel alternative method for the synthesis of internucleotide phosphate bridge, bearing sulfur or selenium atoms. Mechanistic studies have revealed metaphosphate analogues as the probable intermediates, involved in the reactions.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, S-106 91 Stockholm, Sweden.
authors.forename: Marcin
authors.initials: M
authors.lastname: Kalek
authors.forename: Agnieszka
authors.initials: A
authors.lastname: Bartoszewicz
authors.forename: Jacek
authors.initials: J
authors.lastname: Stawinski
mesh_terms: D004951:Esterification; D007455:Iodine / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000737:chemistry*; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D063065:Organophosphonates; D016566:Organoselenium Compounds; D013872:Thionucleosides; D007455:Iodine