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Synthesis of 2-Deoxy-2-fluoro-2-C-methyl-D-ribofuranoses.

✍ Scribed by Jeremy L. Clark; J. Christian Mason; Ann J. Hobbs; Laurent Hollecker; Raymond F. Schinazi

Publisher
John Wiley and Sons
Year
2007
Weight
35 KB
Volume
38
Category
Article
ISSN
0931-7597

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📜 SIMILAR VOLUMES

Labeled 2-deoxy-D-glucose analogs. 18F-l
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## Abstract A convenient method for the synthesis of ^18^F‐2‐deoxy‐2‐fluoro‐D‐glucose (4) and ^18^F‐2‐deoxy‐2‐fluoro‐D‐mannose (8) by the direct fluorination of 3,4,6‐tri‐0‐acetyl‐D‐glucal with ^18^F‐F~2~ is described. ^14^C‐2‐deoxy‐2‐fluoro‐D‐glucose has been synthesized from ^14^C‐3,4,6‐tri‐0‐ace

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The reaction of [2-14C]-2 ,4-bis-O-(trimethylsilyl)uracil (2) with ~-~-acetyl-~-0-benzoyl-2-deoxy-2-fluoro-~-D-arabinofuranosyl bromide (3) yielded the 3-O-acety1-5-0-benzoyl nucleos e 4 which was hydrolyzed with methanolic ammonia to afford [ 2-feC]-T-( 2-deoxy-2fluoro-p-D-arabinofuranosy1)uracil (

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The synthesis of t h e title canpound (7) is described. [2-14C] cytosine (I) is treated with an aqueous mixture of sodium bisulfite and sodium sulfate at 8OoC for 30 rnin. The resulting solid is then treated with aqueous sodiun hydroxide and passed through a cation exchange colunn, producing [ Z-14C

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## Abstract Synthesis of 2′‐deoxy‐2′‐[^18^F]fluoro‐5‐methyl‐1‐__β__‐D‐arabinofuranosyluracil ([^18^F]‐FMAU) is reported. 2‐Deoxy‐2‐[^18^F]fluoro‐1,3,5‐tri‐O‐benzoyl‐__α__‐D‐arabinofuranose **2** was prepared by the reaction of the respective triflate **1** with tetrabutylammonium[^18^F]fluoride. Th

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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