Diastereocontrolled synthesis of phosphorothioate DNA via an oxazaphospholidine approach using a novel class of activators, dialkyl(cyanomethyl)ammonium salts.
Dialkyl(cyanomethyl)ammonium salts 1 were synthesized and used as a novel class of activators for the stereospecific condensations of diastereopure nucleoside 3'-O-oxazaphospholidines with a nucleoside. This new oxazaphospholidine method could efficiently produce both (Rp)- and (Sp)-dinucleoside phosphorothioates.
Oka
Natsuhisa
N
Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Kashiwa, Chiba, Japan.
Wada
Takeshi
T
Saigo
Kazuhiko
K
D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis; D007202:Indicators and Reagents; D010080:Oxazoles; D010710:Phosphates; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis*; D013237:Stereoisomerism
D003853:Deoxyribonucleosides; D007202:Indicators and Reagents; D010080:Oxazoles; D010710:Phosphates; D000644:Quaternary Ammonium Compounds; C083120:phosphorodithioic acid; D004247:DNA