The synthesis of 2-[F-18]fluoro-2-deoxy-D-glucose using glycals: a reexamination

Abstract

The reaction of [F-18]F2 with D-glucal in water proceeds sufficiently mildly at room temperature to present marked regiospecificity. After hydrolysis, analysis by Fourier-transform 19F-NMR showed the product to consist of a mixture of 2-fluoro-2-deoxy-D-glucose (2-FDG) and 2-fluoro-2-deoxy-D-mannose (2-FDM) in a 2:1 ratio, respectively. The presence of the mannose isomer has been revealed by extension of the 19F-NMR analyses to other literature methods for 2-FDG synthesis involving the electrophilic fluorinating agent acetyl hypofluorite. Reaction of acetyl [F-18] hypofluorite, prepared by the reaction of [F-18]F2 with solid sodium acetate trihydrate, with the appropriate glycal/solvent combination, followed by hydrolysis, has led to production of [F-18]2-FDG with a radiochemical purity of 95%.