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

Add time:07/22/2019    Source:sciencedirect.com

5′-O-Dimethoxytrityl deoxyribonucleoside 3′-O-phosphorbisdiethylamidites were prepared by the selective phosphitylation of 5′-O-dinethoxytrityl deoxyribonucleosides with tris(diethylamino)phosphine in the presence of amino and tetrazole as catalyst. The bisamidites activated by p-nitrophenyltetrazole can be coupled efficiently with 5′-hydroxyl group of nucleoside on a solid support. Oligodeoxyribonucleotides were obtained in high yields. The phosphorodiethylamidate linkage was obtained by non-aqueous oxidation using tert-butyl hydroperoxide of the phosphordiethylamidite formed after the coupling.

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