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A rapid synthesis of 2‐deoxy‐2‐fluoro‐d‐glucose from xenon difluoride suitable for labelling with 18 F
Author(s) -
Shiue ChyngYann,
Wolf Alfred P.
Publication year - 1983
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580200202
Subject(s) - xenon difluoride , chemistry , yield (engineering) , difluoride , ether , hydrolysis , fluoride , chemical synthesis , radiochemistry , labelling , glucal , nuclear chemistry , medicinal chemistry , organic chemistry , inorganic chemistry , catalysis , biochemistry , materials science , metallurgy , in vitro
A rapid synthesis of 2‐deoxy‐2‐fluoro‐D‐glucose (3) from xenon difluoride is described. Reaction of 3,4,6‐tri‐O‐acetyl‐D‐glucal (1) with xenon difluoride in ethyl ether in the presence of BF 3 ·OEt 2 for 20 minutes gave 2‐deoxy‐2‐fluoro‐ 3,4,6‐tri‐O‐acetyl‐D‐glucopyranosyl fluoride (2) in 70‐80% chemical yield. Hydrolysis of 2 with 2 N HCl gave 2‐deoxy‐2‐fluoro‐D‐glucose (3) in 50% overall chemical yield in a synthesis time of 60 minutes. Preliminary results indicate that this method can be used to synthesize 2‐deoxy‐2‐ [ 18 F] fluoro‐D‐glucose.