Stereoselective synthesis of dinucleoside phosphorothioate using enantiopure 1,2-amino alcohols as chiral auxiliaries.
Diastereopure nucleoside 3'-cyclic phosphoramidites were synthesized stereoselectively from enantiopure 1,2-amino alcohols. In the presence of a novel activator, these phosphoramidites underwent the condensation with 3'-O-tert-butyldimethylsilylthymidine to give the corresponding phosphite intermediates. Upon sulfurization, followed by deprotection, dithymidine phosphorothioate was obtained in good yield with good to excellent diastereoselectivity.
Oka
N
N
Department of Integrated Biosciences, Graduate School of Frontier Sciences, University of Tokyo, FSB-702, Kashiwanoha, Kashiwa 277-8562, Japan.
Wada
T
T
Saigo
K
K
D000605:Amino Alcohols / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D009946:Organothiophosphorus Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013873:Thionucleotides
D000605:Amino Alcohols; D009838:Oligodeoxyribonucleotides; D009946:Organothiophosphorus Compounds; D013873:Thionucleotides; C476349:dithymidine phosphorothioate