ChemInform Abstract: Reaction of 1,2-Anhydro-3,4:5,6-di-O-isopropylidene-1-C-nitro-D-mannitol with Potassium Hydrogenfluoride in Ethylene Glycol: A Synthesis of 2-Deoxy-2-fluoro-D-glucose.

ChemInform Abstract

Oxidation of the known nitroalkene (I) yields the anhydromannitol (II) as the main product, which is converted to the epimeric fluoro aldehydes (III). Cleavage of the acetal groups in (III) and subsequent acetylation produce the protected fluoropyranoses (IV). O-Deacylation of (IVa) gives 2-deoxy-2-fluoro-D-glucose (V). (IR-, UV-, ¹H-, ¹⁹F-NMR- data).