Highly stereoselective synthesis of (2'R)-[2'-2H]-deoxyribonucleosides and synthesis of their oligonucleotides.
Highly stereoselective synthesis of (2'R)-[2'-2H]-2'-deoxyribonucleosides (2'R:2'S = > 99:1) were accomplished by treating 2'-bromo-3',5'-O-TPDS-2'-deoxyribonucleosides with tributyltin deuteride at lower temperatures such as -60 degrees C in the presence of triethylborane. Moreover, synthesis of some oligodeoxyribonucleosides involving them will be described.
Kawashima
E
E
Laboratory of Pharmaceutical Chemistry, Tokyo College of Pharmacy, Japan.
Sekine
T
T
Miyahara
M
M
Aoyama
Y
Y
Hirao
I
I
Kainosho
M
M
Kyogoku
Y
Y
Ishido
Y
Y
D001880:Boranes / Q000737:chemistry; D003853:Deoxyribonucleosides / Q000138:chemical synthesis*; D009841:Oligonucleotides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014220:Trialkyltin Compounds / Q000737:chemistry
D001880:Boranes; D003853:Deoxyribonucleosides; D009841:Oligonucleotides; D014220:Trialkyltin Compounds; C011559:tributyltin; C079756:triethylborane