Studies of specifically fluoridated carbohydrates. Part V. Derivatives of 3,6-anhydro-5-deoxy-5-fluoro-1,2-O-isopropylidene-α-L-idofuraeose

Abstract

The facile synthesis of 3,6-anhydro-5-deoxy-5-fluoro-1,2-O-isopropylidene-α-L-idofuranose (4) from readily available precursors is described. The 1H and 19F nuclear magnetic resonance spectra of this derivative have been analyzed. Interestingly, the fluorine substituent exhibits detectable spin coupling with all ring protons except H-2. Both of the anomeric 1,2-di-O-acetyl derivatives of (4) have also been studied.