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A simple synthesis of 2-deoxy-2-fluoro-d-galactose using xenon difluoride

โœ Scribed by Christoph C. Geilen; Nikolaus Loch; Werner Reutter; Konrad Seppelt; Franz Oberdorfer


Publisher
Elsevier Science
Year
1992
Tongue
French
Weight
242 KB
Volume
33
Category
Article
ISSN
0040-4039

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## Abstract A rapid synthesis of 2โ€deoxyโ€2โ€fluoroโ€Dโ€glucose **(3)** from xenon difluoride is described. Reaction of 3,4,6โ€triโ€Oโ€acetylโ€Dโ€glucal **(1)** with xenon difluoride in ethyl ether in the presence of BF~3~ยทOEt~2~ for 20 minutes gave 2โ€deoxyโ€2โ€fluoroโ€ 3,4,6โ€triโ€Oโ€acetylโ€Dโ€glucopyranosyl fluo

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SUlMARY 2-Deoxy-2-[1eFlfluoro-D-galactose was prepared using gaseous [ ' a F] acetyl hypofluorite or [ l a FIFz and tri-0-acetyl-0-galactal as substrate. The product was obtained in a surprisingly high epimeric purity ( > g o % ) , even with [ l a P I F ~ as fluorinating reagent, as demonstrated by

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18F labelled compounds. Thus, a synthetic route to ("F)2-Deoxy-2-fluoro-~glucose was studied which should run as simple and hot-cell-friendly as possible and shc~uld deliver the sugar with high yield and free of diastereomers, even by use of high I8F acitivities