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Alternative synthesis of no‐carrier‐added 2‐deoxy‐2‐[ 18 F]fluoro‐D‐glucose using [ 18 F] fluoride ion
Author(s) -
Haradahira Terushi,
Maeda Minoru,
Kojima Masaharu
Publication year - 1988
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.2580250504
Subject(s) - chemistry , fluoride , hydrolysis , yield (engineering) , acetonitrile , nucleophile , medicinal chemistry , ion , nuclear chemistry , potassium fluoride , inorganic chemistry , catalysis , organic chemistry , materials science , metallurgy
Two alternative routes to no‐carrier‐added synthesis of 2‐deoxy‐2‐[ 18 F]fluoro‐D‐glucose (2‐ 18 FDG) involving nucleophilic displacements of methyl 3‐O‐benzyl‐4,6‐O‐benzylidene‐2‐O‐(trifluoromethanesulfonyl) ‐β‐D‐mannopyranoside ( 1 ) and 1,6‐anhydro‐3, 4‐di‐O‐benzyl‐2‐O‐(trifluoromethanesulfonyl)‐β‐D‐mannopyranose ( 2 ) are described. The triflates ( 1 and 2 ) reacted with aminopolyether (Kryptofix 222) supported potassium [ 18 F]fluoride and tetra‐n‐butylammonium [ 18 F]fluoride in acetonitrile to give methyl 3‐O‐benzyl‐4,6‐O‐benzylidene‐2‐deoxy‐2‐[ 18 F] fluoro‐β‐D‐glucopyranoside ( 3 ) and 1,6‐anhydro‐3,4‐di‐O‐benzyl‐2‐deoxy‐2‐[ 18 F] fluoro‐β‐D‐glucopyranose ( 4 ), respectively. The displacement yield with 1 was consistently higher than that with 2 . Hydrolysis of 3 with 6N HCl, followed by passage through an ion retardation resin column and a neutral alumina column, gave 2‐ 18 FDG in 34–43% overall radiochemical yield without correction for decay. Removal of the protecting groups from 4 with 6N HCl or 50% CH 3 SO 3 H led to incomplete hydrolysis. The total preparation time was about 80 min from start of the radiofluorination.