Stereospecific approach to the synthesis of (/sup 18/F)12-deoxy-2-fluoro-D-mannose

Conference · Wed May 01 04:00:00 EDT 1985 · J. Nucl. Med.; (United States)

OSTI ID:6759345

Luxen, A; Barrio, J R; Bida, G T; Satyamurthy, N

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-
• Conference Information: Journal Name: J. Nucl. Med.; (United States) Journal Volume: 26:5
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400201 -- Chemical & Physicochemical Properties
400700 -- Radiochemistry & Nuclear Chemistry
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ACETONE
ACETONITRILE
ALDEHYDES
AMMONIUM COMPOUNDS
AMMONIUM FLUORIDES
ANTIMETABOLITES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CARBOHYDRATES
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
CHROMATOGRAPHY
COMPLEXES
DECOMPOSITION
DIAGNOSTIC TECHNIQUES
DRUGS
FLUORIDES
FLUORINE 18
FLUORINE 19
FLUORINE COMPLEXES
FLUORINE COMPOUNDS
FLUORINE ISOTOPES
FLUORODEOXYGLUCOSE
FOURIER TRANSFORM SPECTROMETERS
HALIDES
HALOGEN COMPOUNDS
HEXOSES
HOURS LIVING RADIOISOTOPES
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYDROLYSIS
INJECTION
INORGANIC ACIDS
INTAKE
ISOTOPES
KETONES
LABELLED COMPOUNDS
LIGHT NUCLEI
LIQUID COLUMN CHROMATOGRAPHY
LYSIS
MAGNETIC RESONANCE
MANNOSE
MEASURING INSTRUMENTS
MEDIUM TEMPERATURE
METHYLENE CHLORIDE
MONOSACCHARIDES
NITRILES
NUCLEAR MAGNETIC RESONANCE
NUCLEI
ODD-EVEN NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC CHLORINE COMPOUNDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
PURIFICATION
RADIOCHEMISTRY
RADIOISOTOPES
RADIOPHARMACEUTICALS
REACTION INTERMEDIATES
RESONANCE
SACCHARIDES
SEPARATION PROCESSES
SOLVOLYSIS
SPECTROMETERS
STABLE ISOTOPES
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SULFONIC ACIDS
SYNTHESIS
TIME DEPENDENCE
TOMOGRAPHY
YIELDS