Synthesis of [18F]-6-deoxy-6-fluoro-D-glucose ([ 18F]6FDG), a potential tracer of glucose transport

Abstract

With the goal of developing a PET radioligand for the in vivo assessment of glucose transport, 6-deoxy-6-[18F]fluoro-D-glucose ([ 18F]6FDG) was prepared in two steps from 18F-. Starting with D-glucose, the tosyl- and mesyl-derivatives of 3,5-O-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose were prepared by known methods. Reaction of either of these precursors with 18F - resulted in the formation of 3,5-O-benzylidene-6-deoxy-O-[ 18F]-fluoro-1,2-O-isopropylidene-α-D-glucofuranose in high yield. Subsequent hydrolysis resulted in the production of [18F]6FDG. Under optimal conditions, [18F]6FDG is produced 60-70 min after end of bombardment (EOB) in 71 ± 12% yield (decay corrected, based upon fluoride) with a radiochemical purity of ≥96%. Preliminary experiments have indicated that [18F]6FDG may be a more representative in vivo tracer for the glucose transporter than 2FDG. Copyright © 2005 John Wiley & Sons, Ltd.