Selective removal of the 2'- and 3'-O-acyl groups from 2',3',5'-tri-O-acylribonucleoside derivatives with lithium trifluoroethoxide.
Selective cleavage of O2' and O3' ester groups from ribonucleoside derivatives has been accomplished with Dowex 1 x 2 (CF3CH2O-) in 2,2,2-trifluoroethanol (TFE) or lithium trifluoroethoxide/TFE. Deacylations with Li+ -OCH2CF3/TFE proceed at ambient temperature (or with mild heating) to give the 5'-O-acyl derivatives in superior yields and higher purity than prior approaches for selective O2' and O3' ester deprotection.
Nowak
Ireneusz
I
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
Jones
Carl T
CT
Robins
Morris J
MJ
D000215:Acylation; D018020:Lithium Compounds / Q000737:chemistry*; D015394:Molecular Structure; D012263:Ribonucleosides / Q000737:chemistry*
C519211:2',3',5'-tri-O-acylribonucleoside; D018020:Lithium Compounds; D012263:Ribonucleosides