title: Preparation of nucleoside H-phosphonoselenoate monoesters via the phosphinate approach.
abstract: An efficient entry to nucleoside 3'-H-phosphonoselenoate monoesters via phosphinate intermediates was developed. It involves a reaction of suitably protected nucleosides with triethylammonium phosphinate in the presence of pivaloyl chloride, followed by selenization of the intermediate nucleoside phosphinates with triphenylphosphine selenide, to produce the corresponding nucleoside H-phosphonoselenoates in 86-92% yields.
authors.affiliation: Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
authors.forename: Martin
authors.initials: M
authors.lastname: Kullberg
authors.forename: Jacek
authors.initials: J
authors.lastname: Stawinski
mesh_terms: D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D063065:Organophosphonates / Q000138:chemical synthesis* / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry*; D018036:Selenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D009705:Nucleosides; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D018036:Selenium Compounds; C061896:triphenylphosphine