182245-84-7Relevant academic research and scientific papers
The case for the intermediacy of monomeric metaphosphate analogues during oxidation of H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters: Mechanistic and synthetic studies
Bartoszewicz, Agnieszka,Kalek, Marcin,Stawinski, Jacek
, p. 5029 - 5038 (2008/12/20)
(Chemical Equation Presented) Studies on the reaction of H-phosphonothioate, H-phosphonodithioate, and H-phosphonoselenoate monoesters with iodine in the presence of a base led to identification of a unique oxidation pathway, which consists of the initial oxidation of the sulfur or selenium atom in these compounds, followed by oxidative elimination of hydrogen iodide to generate the corresponding metaphosphate analogues. The intermediacy of the latter species during oxidation of the investigated H-phosphonate monoester derivatives with iodine was supported by various diagnostic experiments. The scope and limitation of these oxidative transformations for the purpose of the synthesis of nucleoside phosphorothioate, nucleoside phosphorodithioate, and nucleoside phosphoroselenoate diesters was also investigated.
New methods for multiple modifications of a phosphorus centre. Their relevance to nucleotide and oligonucleotide analogues synthesis
Kers, Inger,Cieslak, Jacek,Jankowska, Jadwiga,Kraszewski, Adam,Stawinski, Jacek
, p. 1245 - 1246 (2007/10/03)
Nucleoside phosphoramidates and their analogues with the P-N bond in bridging positions of the phosphoramidate linkage were prepared by a new method utilizing the corresponding pyridine adducts of metaphosphates. Also, a new procedure was developed for the synthesis of unprotected nucleoside phosphoromono- and phosphorodithioates.
A new synthetic method for the preparation of nucleoside phosphoramidate analogues with the nitrogen atom in bridging positions of the phosphoramidate linkage
Kers, Inger,Stawinski, Jacek,Kraszewski, Adam
, p. 1219 - 1222 (2007/10/03)
An efficient method for the preparation of nucleoside P3' → N5' and N3' → P5' phosphoramidates and their thio analogues results from generation of a pyridine adduct of a nucleoside metaphosphate or its analogue from a nucleoside H-phosphonate, nucleoside H-phosphonothioate or nucleoside H-phosphonodithioate monoester followed by its reaction with 5'- or 3'-aminonucleoside.
A facile access to nucleoside phosphorofluoridate, nucleoside phosphorofluoridothioate, and nucleoside phosphorofluoridodithioate monoesters
Bollmark, Martin,Stawinski, Jacek
, p. 5739 - 5742 (2007/10/03)
Oxidation of H-phosphonate, H-phosphonothioate, or H-phosphonodithioate monoesters with iodine in pyridine in the presence of trimethylsilyl chloride, followed by addition of triethylamine trishydrofluoride (TAF) furnished rapid and quantitative formation of the corresponding phosphorofluoridate, phosphorofluoridothioate, or phosphorofluoridodithioate monoesters.
