Solid-phase stereoselective synthesis of 2'-O-methyl-oligoribonucleoside phosphorothioates using nucleoside bicyclic oxazaphospholidines.
The use of 2'-OMe-ribonucleoside bicyclic oxazaphospholidines derived from (R)- or (S)-2-pyrrolidinemethanol has enabled the stereoselective synthesis of (Rp)-, and (Sp)-2'-O-methyloligoribonucleoside phosphorothioates. Interestingly, higher stereoselectivity (96-98%) was observed in the synthesis of (Sp)-2'-O-methyl-oligoribonucleoside phosphorothioates compared to that in the case of (Sp)-oligodeoxyribonucleoside phosphorothioates (90%).
Guo
M
M
Hybridon Inc., Cambridge, MA 02139, USA.
Yu
D
D
Iyer
R P
RP
Agrawal
S
S
D002851:Chromatography, High Pressure Liquid; D015195:Drug Design; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D009843:Oligoribonucleotides / Q000138:chemical synthesis*; D063086:Organothiophosphates / Q000138:chemical synthesis*; D013237:Stereoisomerism
D009843:Oligoribonucleotides; D063086:Organothiophosphates