Some novel pyrimidine nucleoside rearrangements effected by diethylaminosulfur trifluoride (DAST). |
| |
| Authors: | A E Lloyd P L Coe O W Howarth R T Walker |
| |
| Institution: | School of Chemistry, University of Birmingham, UK. |
| |
| Abstract: | 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. |
| |
| Keywords: | |
|
|
