The development of synthetic methodology for a short radiosynthesis of 2-deoxy-2-[18F]fluororibose (2-FDR) is presented. Radiolabeled analogs of sugars have wide applications as Positron Emission Tomography (PET) tracers for imaging of cell proliferation and heart and brain functions. Several synthetic challenges in the radiosynthesis of 2-FDR arose; for example, the protecting group on the C-3 hydroxyl, trans to a leaving group at C-2, hinders that position from the SN2 attack by fluoride. Also the stabilization of carbocations at C-2 via anchimeric assistance by the group at C-3 caused various skeletal rearrangements and non-stereoselective fluorination. In order to overcome these hurdles, we installed the completely non-participating p-nitrobenzyl (PNBn) protecting group on the hydroxyl group at C-3. Stereoselective fluorination at C-2 under standard fluorination conditions preceded in high yield within 60 min. Reductive deprotection-hydrolysis of the PNBn groups was complete in 30 min. All manipulations were finished in less than two hours. Radiolabeled probe was utilized for the quantitative determination of need for liver transplant due to its functional failure. The details of this investigation will be described at the meeting.

Radiosynthesis of 2-deoxy-2-[18F]-fluororibose, a new positron emission tomography probe

248th National Meeting (2014)

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