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Synthesis of 3 '-deoxy-3'-fluorothymidine (FLT) 5 '-O-glucuronide: a reference standard for imaging studies with [¹⁸F]FLT

Lookup NU author(s): Dr Suzannah HarnorORCiD, Dr Tommy Rennison, Dr Martin Galler, Dr Celine CanoORCiD, Professor Roger Griffin, Professor Herbie Newell, Emeritus Professor Bernard Golding

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Abstract

Reaction of methyl 2,3,4-tri-O-acetyl-1-O-(trichloroacetimidoyl)-alpha-D-glucopyranuronate with 3'-deoxy-3'-fluorothymidine in the presence of trimethylsilyl trifluoromethanesulfonate gave (2R,3R,4S,5S,6S)2-((( 2R,3S,5R)-3-fluoro-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)-methoxy)-6-(methoxycarbonyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate, which was hydrolysed to 3'-deoxy-3'-fluorothymidine-5'-glucuronide. Analysis of this reference standard by high performance liquid chromatography enabled the identification of [F-18]3'-deoxy-3'-fluorothymidine-5'-glucuronide in blood samples from six human patients who had been administered [F-18]3'-deoxy-3'-fluorothymidine.

Publication metadata

Author(s): Harnor SJ, Rennison T, Galler M, Cano C, Griffin RJ, Newell DR, Golding BT

Publication type: Article

Publication status: Published

Journal: MedChemComm

Year: 2014

Volume: 5

Issue: 7

Pages: 984-988

Print publication date: 01/01/2014

ISSN (print): 2040-2503

ISSN (electronic): 2040-2511

Publisher: Royal Society of Chemistry

URL: http://dx.doi.org/10.1039/c3md00381g

DOI: 10.1039/c3md00381g

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