104655-76-7Relevant academic research and scientific papers
The 3-(N-tert-butylcarboxamido)-1-propyl group as an attractive phosphate/thiophosphate protecting group for solid-phase oligodeoxyribonucleotide synthesis
Wilk, Andrzej,Chmielewski, Marcin K.,Grajkowski, Andrzej,Phillips, Lawrence R.,Beaucage, Serge L.
, p. 6430 - 6438 (2007/10/03)
Among the various phosphate/thiophosphate protecting groups suitable for solid-phase oligonucleotide synthesis, the 3-(N-tert-butylcarboxamido)-1-propyl group is one of the most convenient, as it can be readily removed, as needed, under thermolytic conditions at neutral pH. The deprotection reaction proceeds rapidly (t1/2 ～ 100 s) through an intramolecular cyclodeesterification reaction involving the amide function and the release of the phosphate/thiophosphate group as a 2-(tertbutylimino)tetrahydrofuran salt. Incorporation of the 3-(N-tert-butylcarboxamido)-1-propyl group into the deoxyribonucleoside phosphoramidites 1a-d is achieved using inexpensive raw materials. The coupling efficiency of 1a-d in the solid-phase synthesis of d(ATCCGTAGCTAAGGTCATGC) and its phosphorothioate analogue is comparable to that of commercial 2-cyanoethyl deoxyribonucleoside phosphoramidites. These oligonucleotides were phosphate/thiophosphate-deprotected within 30 min upon heating at 90 °C in Phosphate-Buffered Saline (PBS buffer, pH 7.2). Since no detectable nucleobase modification or significant phosphorothioate desulfurization occurs, the 3-(N-tert-butylcarboxamido)-1-propyl group represents an attractive alternative to the 2-cyanoethyl group toward the large-scale preparation of therapeutic oligonucleotides.
A simple Preparation of 5'-O-dimethoxytrityl Deoxyribonucleoside 3'-O-Phosphorbisdiethylamidites as Useful Intermediates in the Synthesis of Oligodeoxyribonucleotides and Their Phosphorodiethylamidate Analogs on a Solid Support
Yamana, Kazushige,Nishijima, Yoshitaka,Oka, Atsushi,Nakano, Hidehiko,Sangen, Osamu,et al.
, p. 4135 - 4140 (2007/10/02)
5'-O-Dimethoxytrityl deoxyribonucleoside 3'-O-phosphorbisdiethylamidites were prepared by the selective phosphitylation of 5'-O-dimethoxytrityl deoxyribonucleosides with tris(diethylamino)phosphine in the presence of amine and tetrazol as catalyst.The bisamidites activated by p-nitrophenyltetrazole can be coupled efficiently with 5'hydroxyl group of nucleoside on a solid support.Oligodeoxyribonucleotides were obtined in high yields.The phosphorodiethylamidate linkage was obtained by non-aqueous oxidation using tert-butyl hydroperoxyde of the phosphordiethylamidite formed after the coupling.
Deoxyribonucleoside Phosphorodithioates. Preparation of Dinucleoside Phosphorodithioates from Nucleoside Thiophosphoramidites
Dahl, Bjarne H.,Bjergarde, Kirsten,Sommer, Vibeke B.,Dahl, Otto
, p. 896 - 901 (2007/10/02)
A series of protected thymidine thiophosphoramidites have been prepared and their properties evaluated.Although less reactive than phosphoramidites, thiophosphoramidites with small N-substituents (methyl) are useful synthons for the preparation of nucleoside phosphorodithioates, as demonstrated by the preparation of a thymidine dimer.The coupling reactions are not as clean as those of the analogous phosphoramidites since the alkylthio group is somewhat labile.
A CONVENIENT AND GENERAL APPROACH TO THE SYNTHESIS OF PROPERLY PROTECTED d-NUCLEOSIDE-3'-HYDROGENPHOSPHONATES VIA PHOSPHITE INTERMEDIATES
Marugg, J. E.,Tromp, M.,Kuyl-Yeheskiely, E.,Marel, G. A. van der,Boom, J. H. van
, p. 2661 - 2664 (2007/10/02)
Evidence will be presented to show that the monofunctional phosphitylating reagents bis(N,N-di-ethylamino)chlorophosphine and salicylchlorophosphine are very effective for the preparation of 5'-O,N-protected d-nucleoside-3'-hydrogenphosphonates.
