Asymmetric synthesis of 6ꢀLꢀthreoꢀ[18F]FDOPS
Russ.Chem.Bull., Int.Ed., Vol. 63, No. 5, May, 2014
1177
for TLC in system 1: [18F]fluoride 0.02; 4,5ꢀmethylenedioxyꢀ2ꢀ
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nitrobenzaldehyde
(1)
0.45;
4,5ꢀmethylenedioxyꢀ2ꢀ
[
18F]fluorobenzaldehyde (4) 0.45; 2ꢀfluoroꢀ4,5ꢀbis(methoxyꢀ
methoxy)benzaldehyde (3) 0.45; 2ꢀ[18F]fluoroꢀ4,5ꢀbis(methoxyꢀ
methoxy)benzaldehyde (5) 0.45. Retention factors (Rf) for TLC
in system 2: [18F]fluoride 0.02; 4,5ꢀmethylenedioxyꢀ2ꢀnitrobenzꢀ
aldehyde (1) 0.65; 4,5ꢀbis(methoxymethoxy)ꢀ2ꢀnitrobenzaldeꢀ
hyde (2) 0.60; 2ꢀfluoroꢀ4,5ꢀbis(methoxymethoxy)benzaldehyde (3)
0.65; 2ꢀ[18F]fluoroꢀ4,5ꢀmethylenedioxybenzaldehyde (4) 0.65;
2ꢀ[18F]fluoroꢀ4,5ꢀbis(methoxymethoxy)benzaldehyde (5) 0.65;
Niꢀ(R)ꢀBPBꢀ(S)ꢀthreoꢀ6ꢀFDOPS(OCH2O) (10) 0.25; Niꢀ(R)ꢀ
BPBꢀ(S)ꢀthreoꢀ6ꢀ[18F]FDOPS(OCH2O) (6) 0.25; Niꢀ(R)ꢀBPBꢀ
(S)ꢀthreoꢀ6ꢀFDOPS(OMOM)2 (9) 0.25; Niꢀ(R)ꢀBPBꢀ(S)ꢀthreoꢀ
6ꢀ[18F]FDOPS(OMOM)2 (7) 0.25. Retention factors (Rf) for
TLC in system 3: [18F]fluoride 0.02; 4,5ꢀmethylenedioxyꢀ2ꢀ
nitrobenzaldehyde (1) 0.65; 2ꢀ[18F]fluoroꢀ4,5ꢀmethylenedioxyꢀ
benzaldehyde (4) 0.65; 6ꢀLꢀthreoꢀ[18F]FDOPS (8) 0.40.
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Analysis by HPLC. The target product was analyzed by raꢀ
dioꢀHPLC on a column Lichrospher C18 (5 m, 250×4.6 mm)
under the following conditions: eluent 0.1% AcOH, the flow rate
1.0 mL min–1; detection of nonradioactive standard 6ꢀLꢀthreoꢀ
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ka, A. J. Luxen, C. F. Lemaire, J. Nucl. Med., 2013, 54, 1.
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[
19F]FDOPS (obtained in situ by decomposition of complex 9):
254 nm, retention time 7.1 min. Retention time of complex 8
(7.6 min) was determined using a flow detector of radioactivity
set up in the line after UV detector.
This work was financially supported by the Russian
Foundation for Basic Research (Project RFBRꢀTaiwan
No. 11ꢀ04ꢀ92010/13).
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Received November 19, 2013;
in revised form April 8, 2014