Stereocontrolled synthesis of dinucleoside boranophosphates by an oxazaphospholidine method.
Stereodefined dinucleoside boranophosphates were synthesized from diastereopure nucleoside 3'-oxazaphospholidine derivatives. The new method is based on the stereospecific formation of dinucleoside phosphite intermediates catalyzed by a non-nucleophilic acidic activator, N-(cyanomethyl)pyrrolidinium triflate, and the boronation of the intermediates.
Oka
Natsuhisa
N
Department of Medical Genome Sciences, Graduate School of Frontier Sciences, The University of Tokyo, 5-1-5 Kashiwanoha, Kashiwa, Chiba 277-8562, Japan.
Maizuru
Yukihiro
Y
Shimizu
Mamoru
M
Saigo
Kazuhiko
K
Wada
Takeshi
T
D001671:Biochemistry / Q000379:methods; D001880:Boranes / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D015226:Dinucleoside Phosphates / Q000138:chemical synthesis* / Q000737:chemistry; D010080:Oxazoles / Q000737:chemistry*; D010710:Phosphates / Q000737:chemistry; D013237:Stereoisomerism; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D001880:Boranes; D001896:Boron Compounds; D015226:Dinucleoside Phosphates; D010080:Oxazoles; D010710:Phosphates; C510710:boranophosphate; C107859:dithymidine boranomonophosphate; D013936:Thymidine