Highly chemo- and regioselective phosphitylation of 2'-deoxyribonucleosides.
We developed a novel method for the highly chemo- and regioselective phosphitylation of the 5'-hydroxy group of 2'-deoxyribonuleosides with bis(O-tert-butyl) N,N-diethylphosphoramidite. The tert-butyl groups introduced in the thymidine 5'-O-phosphite and 2'-deoxycytidine 5'-O-phosphite were simultaneously removed within 5 min by treatment with trimethylsilyl triflate in acetonitrile to give the corresponding H-phosphonate monoesters without any side reactions.
D003853:Deoxyribonucleosides / Q000737:chemistry*; D017905:Phosphites / Q000737:chemistry*
D003853:Deoxyribonucleosides; D017905:Phosphites