A. E. Lloyd, P. Coe, R. Walker
Feb 1, 1993
Citations
0
Influential Citations
16
Citations
Journal
Journal of Fluorine Chemistry
Abstract
Abstract Treatment of methyl 2,3- O -isopropylidene-β- D -ribofuranoside with DAST gave a goodyield of 2,3- O -isopropylidene-5- O -methyl-β- D -ribofuranosyl fluoride in which the methoxygroup had migrated from C-1 → C-5 and been replaced with retention of configurationby fluorine. The corresponding aldehyde when treated under similar conditions underwenta similar migration to give 5-deoxy-5-fluoro-2,3- O -isopropylidene-5- O -methyl-β- D -ribofuranosylfluoride. A similar migration occurred with methyl 2′,3′-di- O -acetyl-β- D -ribofuranosideand with acetyl 2,3- O -isopropylidene - D -ribofuranose but not with 1,2,3-tri- O -acetyl- D -ribofuranose. Thus the migration depends upon the migratory aptitude of thesubstituent at C-1 and the conformation of the furanose ring. Two ribofuranosyl fluorideswere used as starting materials from which to make nucleosides by the method of Noyoriand Hayoshi.