Process for preparing dithiophosphate oligonucleotide analogs via nucleoside thiophosphoramidite intermediates

作者: Nassar Farschtschi , David Gorenstein

DOI:

关键词:

摘要: A method for synthesis of oligonucleotide analogs having dithiophosphate internucleosidic linkages is described. Monohalohydrocarbylthiophosphoramidites are utilized to prepare nucleoside thiophosphoramidite intermediates which activated coupling with tetrazole catalysts. Sulfur oxidation and dehydrocarbylation the coupled thiophosphite provide achiral linkages.

参考文章(6)
Nasser Farschtschi, David G. Gorenstein, Preparation of a deoxynucleoside thiophosphoramidite intermediate in the synthesis of nucleoside phosphorodithioates Tetrahedron Letters. ,vol. 29, pp. 6843- 6846 ,(1988) , 10.1016/S0040-4039(00)88455-5
Wolfgang K. D. Brill, Jin Yan Tang, Yun Xi Ma, Marvin H. Caruthers, Synthesis of oligodeoxynucleoside phosphorodithioates via thioamidites Journal of the American Chemical Society. ,vol. 111, pp. 2321- 2322 ,(1989) , 10.1021/JA00188A066
S.L. Beaucage, M.H. Caruthers, Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis Tetrahedron Letters. ,vol. 22, pp. 1859- 1862 ,(1981) , 10.1016/S0040-4039(01)90461-7
Wolfgang K.-D. Brill, John Nielsen, Marvin H. Caruthers, Synthesis of dinucleoside phosphorodithioates via thioamidites Tetrahedron Letters. ,vol. 29, pp. 5517- 5520 ,(1988) , 10.1016/S0040-4039(00)80801-1
Marvin H. Caruthers, Serge L. Beaucage, Phosphoramidite nucleoside compounds ,(1984)