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Mol Imaging Biol. 2004 Sep-Oct;6(5):324-30.

Practical and reliable synthesis of 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose, a precursor of 2-deoxy-2-[18F]fluoro-D-glucose (FDG).

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  • 1Crump Institute of Molecular Imaging and LA Tech Center, Department of Molecular and Medical Pharmacology, David Geffen School of Medicine at University of California, Los Angeles, CA 90230, USA.

Erratum in

  • Mol Imaging Biol. 2004 Nov-Dec;6(6):417.



To develop a practical and reliable synthesis of 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-beta-D-mannopyranose (mannose triflate), a precursor of 2-deoxy-2-[18F]fluoro-D-glucose (FDG).


The key intermediate in the preparation of the triflate precursor, 1,3,4,6-tetra-O-acetyl-beta-D-mannopyranose, was synthesized starting from D-mannose via the following four steps: (1) per-O-acetylation with Ac2O-I2, (2) formation of acetobromomannose with 30% HBr in AcOH, (3) 1,2-orthoester formation with EtOH-2,4,6-collidine and (4) hydrolysis of the 1,2-orthoester with 1M aqueous HCl. Triflation of this key intermediate with Tf2O-pyridine then completed the synthesis of the mannose triflate.


Starting from 200 g of D-mannose, the triflate precursor was synthesized with an overall yield of 65 g to 85 g (12% to 16%) in approximately seven days. The inherent low efficiency of the orthoester hydrolysis was compensated by the quantitative recovery and subsequent recycling of penta-O-acetyl-D-mannopyranose.


A large-scale preparation of mannose triflate is now routinely carried out to satisfy the growing needs for FDG in both research centers and hospitals.

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