Stereospecific approach to the synthesis of (/sup 18/F)12-deoxy-2-fluoro-D-mannose
The reaction of methyl 4,6-O-benzylidene-3-O-benzyl-2-O- trifluoromethanesulfonyl-..beta..-D-glucopyranoside in acetonitrile at 75/sup 0/ for 30 min with (/sup 18/F)tetra-n-butylammonium fluoride, followed by silica gel column purification (di-chloromethane: acetone, 95:5) gave the corresponding (/sup 18/F) methyl 4,6-O-benzylidene-3-O-benzyl- 2-fluoro- ..beta.. -D-mannopyranoside with complete regio- and stereoselectivity (42% radiochemical yield). Hydrolysis of the radiolabeled fluoromannopyranoside intermediate with either 6N HCl or 50% methanesulfonic acid for 30 min at reflux, followed by purification by column chromatography (ion retardation, AG11A8 resin and neutral alumina) gave pure (/sup 18/F)2-deoxy-2-fluoro-D-mannose ((/sup 18/F) 2-FDM) suitable for human injection with a total radiochemical yield (from (/sup 18/F) fluoride ion) of 34%. Since chromatographic identification of 2-fluorodeoxyhexoses does not necessarily constitute a proof of chemical structure, unequivocal evidence of the identity of the final product was obtained using Fourier transform /sup 19/F-NMR. Samples with sufficient fluorine 19 mass when analyzed using /sup 19/F-NMR spectroscopy (Bruker WM-500, 470.56 MHz) after F-18 decay, showed only two peaks corresponding to the two anomers of 2-FDM (..cap alpha..=38.16, ..beta..=56.56; D/sub 2/O, solvent; C/sub 6/F/sub 6/, external reference; proton decoupled). The synthetic procedure described here permits the routine preparation of large amounts of (/sup 18/F)/sub 2/-FDM for tomographic studies. In this manner, comparisons of the biological and kinetic behavior of epimerically pure (/sup 18/F)2-deoxy-2-fluoro-D-glucose ((/sup 18/F)2-FDG) and (/sup 18/F)2-FDM in humans are now possible.
- Research Organization:
- UCLA School of Medicine, Los Angeles, CA
- OSTI ID:
- 6759345
- Report Number(s):
- CONF-850611-; TRN: 87-010776
- Journal Information:
- J. Nucl. Med.; (United States), Vol. 26:5; Conference: 32. annual meeting of the Society of Nuclear Medicine, Houston, TX, USA, 2 Jun 1985
- Country of Publication:
- United States
- Language:
- English
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37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
FLUORINE 18
RADIOCHEMISTRY
MANNOSE
CHEMICAL PREPARATION
ACETONE
ACETONITRILE
AMMONIUM FLUORIDES
CHEMICAL COMPOSITION
CHEMICAL REACTION YIELD
FLUORINE 19
FLUORINE COMPLEXES
FLUORODEOXYGLUCOSE
FOURIER TRANSFORM SPECTROMETERS
HYDROCHLORIC ACID
HYDROLYSIS
INJECTION
LIQUID COLUMN CHROMATOGRAPHY
MEDIUM TEMPERATURE
METHYLENE CHLORIDE
NUCLEAR MAGNETIC RESONANCE
PURIFICATION
RADIOPHARMACEUTICALS
REACTION INTERMEDIATES
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SULFONIC ACIDS
TIME DEPENDENCE
TOMOGRAPHY
ALDEHYDES
AMMONIUM COMPOUNDS
ANTIMETABOLITES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CARBOHYDRATES
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
COMPLEXES
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DRUGS
FLUORIDES
FLUORINE COMPOUNDS
FLUORINE ISOTOPES
HALIDES
HALOGEN COMPOUNDS
HEXOSES
HOURS LIVING RADIOISOTOPES
HYDROGEN COMPOUNDS
INORGANIC ACIDS
INTAKE
ISOTOPES
KETONES
LABELLED COMPOUNDS
LIGHT NUCLEI
LYSIS
MAGNETIC RESONANCE
MEASURING INSTRUMENTS
MONOSACCHARIDES
NITRILES
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RADIOISOTOPES
RESONANCE
SACCHARIDES
SEPARATION PROCESSES
SOLVOLYSIS
SPECTROMETERS
STABLE ISOTOPES
SYNTHESIS
YIELDS
550601* - Medicine- Unsealed Radionuclides in Diagnostics
400201 - Chemical & Physicochemical Properties
400700 - Radiochemistry & Nuclear Chemistry