Preparation of nucleoside H-phosphonoselenoate monoesters via the phosphinate approach.
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.
Kullberg
Martin
M
Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, Stockholm, Sweden.
Stawinski
Jacek
J
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
D009705:Nucleosides; D063065:Organophosphonates; D009943:Organophosphorus Compounds; D018036:Selenium Compounds; C061896:triphenylphosphine