Some novel pyrimidine nucleoside rearrangements effected by diethylaminosulfur trifluoride (DAST).
Pyrimidine nucleosides (or their 5'-aldehydes) when treated with DAST give O2,5'-(fluoro)-anhydronucleosides. If this is prevented by blocking N-3 or O4, the desired 5'-deoxy-5'-(di)-fluoronucleoside is accompanied by the production of a compound resulting from migration of the base following scission of the N-1-->C-1' bond and formation of O2-->C-5'. This is a particular example of a much more general phenomenon, seen when suitably substituted ribofuranoses are treated with DAST.
Lloyd
A E
AE
School of Chemistry, University of Birmingham, UK.
Coe
P L
PL
Howarth
O W
OW
Walker
R T
RT
D004048:Diethylamines / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D007202:Indicators and Reagents; D009690:Nucleic Acid Conformation; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
D004048:Diethylamines; D007202:Indicators and Reagents; D011741:Pyrimidine Nucleosides; D005461:Fluorine; C040394:diethylaminosulfur trifluoride