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Preparation of Nucleoside H-Phosphonoselenoate Monoesters Via the Phosphinate Approach |
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| Authors: | Martin Kullberg Jacek Stawinsk |
| Affiliation: | 1. Department of Organic Chemistry , Arrhenius Laboratory, Stockholm University , Stockholm, Sweden;2. Department of Organic Chemistry , Arrhenius Laboratory, Stockholm University , Stockholm, Sweden;3. Institute of Bioorganic Chemistry, Polish Academy of Sciences , Poznan, Poland |
| 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. |
| Keywords: | H-Phosphonoselenoate monoesters H-Phosphinates H-Phosphonate approach Triphenylphosphine selenide Triphenyl phosphoroselenoate |