Electrophilic fluorinations with glycals. Effect of solvent and substrate on product distribution

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

OSTI ID:6759279

Bida, G T; Satyamurthy, N; Padgett, H C; Barrio, J R

Recent results for the synthesis of F-18 labeled 2-deoxy-2-fluoro-D-glucose ((F-18)2-FDG) have shown that stereochemical control of the glycal carbon-carbon double bond addition reaction depends upon several factors, including solvent polarity and structure of the substrate. Investigation of the stereochemical course of electrophilic fluorinations with F-18 labeled fluorine (F/sub 2/) and acetyl hypofluorite (AcOF) has been extended to include reactions with the following glycal/solvent combinations: 1) 3,4,6-tri-O-acetyl-D-glucal (TAG) in freon (CFCl/sub 3/), acetic acid and acetonitrile, and 2) D-glucal in water, acetic acid, and acetonitrile. Following hydrolysis of the fluorinated crude mixture (1N HCl, 120/sup 0/C, 10-20 min) and column purification, the products were analyzed by Fourier transform F-19 NMR. Several interesting features have been observed for these reactions. For example, the reaction of D-glucal in acetonitrile with either F/sub 2/ or AcOF yields mainly 2-deoxy-2-fluoro-D-mannose (2-FDM; 2-FDM: 2-FDG approx. =4). In contrast, TAG in freon reacted with ACOF (gas phase) to give nearly pure 2-FDG (-- 95% radiochemical purity). Thus, by appropriate choice of solvent, substrate, and fluorinating agent (F/sub 2/ or AcOF), control over the 2-FDG: 2-FDM ratio can be effected for these reactions.

• Research Organization: UCLA School of Medicine, Los Angeles, CA 90024
• OSTI ID: 6759279
• 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

38 RADIATION CHEMISTRY, RADIOCHEMISTRY, AND NUCLEAR CHEMISTRY
400700 -- Radiochemistry & Nuclear Chemistry
550601* -- Medicine-- Unsealed Radionuclides in Diagnostics
62 RADIOLOGY AND NUCLEAR MEDICINE
ACETIC ACID
ACETONITRILE
ALDEHYDES
ALKALINE EARTH METAL COMPOUNDS
ANTIMETABOLITES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
CALCIUM COMPOUNDS
CALCIUM FLUORIDES
CALCIUM HALIDES
CARBOHYDRATES
CARBOXYLIC ACIDS
CHEMICAL BONDS
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DECOMPOSITION
DRUGS
FLUORIDES
FLUORINATION
FLUORINE 18
FLUORINE COMPOUNDS
FLUORINE ISOTOPES
FLUORITE
FLUORODEOXYGLUCOSE
FOURIER TRANSFORMATION
FREONS
HALIDE MINERALS
HALIDES
HALOGEN COMPOUNDS
HALOGENATED ALIPHATIC HYDROCARBONS
HALOGENATION
HEXOSES
HOURS LIVING RADIOISOTOPES
HYDROCHLORIC ACID
HYDROGEN COMPOUNDS
HYDROLYSIS
INORGANIC ACIDS
INTEGRAL TRANSFORMATIONS
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
LYSIS
MANNOSE
MINERALS
MONOCARBOXYLIC ACIDS
MONOSACCHARIDES
NITRILES
NMR SPECTRA
NUCLEI
ODD-ODD NUCLEI
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PURIFICATION
RADIOACTIVITY
RADIOISOTOPES
RADIOPHARMACEUTICALS
REACTION KINETICS
SACCHARIDES
SOLVOLYSIS
SPECTRA
STEREOCHEMISTRY
STRUCTURAL CHEMICAL ANALYSIS
SUBSTRATES
SYNTHESIS
TRANSFORMATIONS
YIELDS