54921-72-1Relevant articles and documents
Bisphosphonate prodrugs: Synthesis of new aromatic and aliphatic 1-hydroxy-1,1-bisphosphonate partial esters
Monteil, Maelle,Guenin, Erwann,Migianu, Evelyne,Lutomski, Didier,Lecouvey, Marc
, p. 7528 - 7537 (2007/10/03)
Methods for the preparation of various 1-hydroxy-1,1-bisphosphonate partial esters were developed. They were obtained from (alkyl or phenyl) bis(trimethylsilyl) phosphite and aromatic or aliphatic acid chlorides, followed by methanolysis.
High yield protection of purine ribonucleosides for phosphoramidite RNA synthesis
Song, Quanlai,Wang, Weimin,Fischer, Artur,Zhang, Xiaohu,Gaffney, Barbara L.,Jones, Roger A.
, p. 4153 - 4156 (2007/10/03)
We report high yield procedures for protection of purine ribonucleosides based on a reaction which allows concomitant highly regiospecific 2'-silylation and 3'-phosphitylation. Subsequent cleavage of the H-phosphonate monoester moiety without silyl migration provides intermediates ready for phosphitylation by standard methods to give fully protected phosphoramidites.
Use of ammonium aryl H-phosphonates in the preparation of nucleoside H-phosphonate building blocks
Ozola, Vita,Reese, Colin B.,Song, Quanlai
, p. 8621 - 8624 (2007/10/03)
Ammonium 4-methylphenyl H-phosphonate 4c was used in the conversion of 5'-0-(dimethoxy-trityl)-2'-deoxynucleoside derivatives 6 into the corresponding 3'-H-phosphonates 2, which were isolated in a high state of purity and in high yield.
Studies on aryl H-phosphonates. 3. Mechanistic investigations related to the disproportionation of diphenyl H-phosphonate under anhydrous basic conditions
Kers, Annika,Kers, Inger,Stawinski, Jacek,Sobkowski, Michal,Kraszewski, Adam
, p. 9931 - 9944 (2007/10/03)
Diphenyl H-phosphonate undergoes under anhydrous reaction conditions a base-promoted disproportionation to triphenyl phosphite and phenyl H- phosphonate. On the basis of 31P NMR data the most likely mechanism for this transformation was proposed. In order to substantiate these findings and to get a deeper insight into the chemistry of aryl H-phosphonate esters, we carried out also some studies on activation of phenyl and diphenyl H- phosphonates with various condensing agents. We found that aryl vs alkyl esters of phosphonic acid often follow different reaction pathways during the activation, and this can most likely be traced back to higher electrophilicity of the phosphorus centre and to higher reactivity of the P- H bonds in aryl H-phosphonate derivatives.