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Alternative synthesis of no-carrier-added 2-deoxy-2-[18F]fluoro-D-glucose using [18F] fluoride ion

✍ Scribed by Terushi Haradahira; Minoru Maeda; Masaharu Kojima

Publisher
John Wiley and Sons
Year
1988
Tongue
French
Weight
424 KB
Volume
25
Category
Article
ISSN
0022-2135

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✦ Synopsis

Two alternative routes to no-carrier-added synthesis of 2-deoxy-2-[ "F] f luoro-D-glucose (2-18FDG) involving nucleophilic displacements of methyl 3-0-benzyl-4,6-0-benzylidene-2-O-(trifluoromethanesulfonyl~-~-D-mannopyranoside (1) and l,6-anhydro-3,4-di-0-benzyl-2-O-(trifluoromethanesulfonyl)-~-D-mannopyranose (2) are described. The triflates (1 and 2, reacted with aminopolyether (Kryptof ix 222) supported potassium [ "FTf luoride and tetra-n-butylammonium [18F] fluoride in acetonitrile to give methyl 3-0-benzyl-4,6-0-benzylidene- 2-deoxy-2-["F] f luoro-P-D-glucopyranoside (2) and 1,6-anhydro-3,4-di-O-benzyl-2-deoxy-2-f 1 ' F ] f luoro-P-D-glucopyranose ( : ) ,

respectively. The displacement yield with 1 was consistently higher than that with 2. Hydrolysis of 2 with 6N HC1, followed by passage through an ion retardation resin column and a neutral alumina column, gave 2-18FDG in 34-43% overall radiochemical yielc! without correction for decay. Removal of the protecting groups from 4 with 6N HC1 or 50% CH3S03H led to incomplete hydrolysis. The total preparation time was about 80 min from start of the radiofluorination.

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