Format

Send to

Choose Destination
See comment in PubMed Commons below
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).

Author information

  • 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. ttoyokuni@mednet.ucla.edu

Erratum in

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

Abstract

PURPOSE:

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).

PROCEDURES:

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.

RESULTS:

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.

CONCLUSION:

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.

PMID:
15380742
DOI:
10.1016/j.mibio.2004.06.006
[PubMed - indexed for MEDLINE]

LinkOut - more resources

Full Text Sources

Other Literature Sources

PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Loading ...
    Support Center