Factors affecting the purity of 2-fluoro-2-deoxy-D-glucose (2-FDG) synthesized from the reactions of glycals with acetyl hypofluorite (CH/sub 3/CO/sub 2/F)

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

OSTI ID:7030712

Shiue, C Y; Wolf, A P

The 2-/sup 18/FDG has been synthesized either by nucleophilic substitution with /sup 18/F/sup -/ or by electrophilic fluorination with F/sub 2/ or CH/sub 3/CO/sub 2/F. Recently, there are reports that 2-FDG synthesized from electrophilic fluorination contains 2-fluoro-2-deoxy-D-mannose (2-FDM) as an impurity. The authors report here the steric effects and the solvent effects on the stereoselectivity of the reactions of glycals with CH/sub 3/CO/sub 2/F. Reactions of glycals with CH/sub 3/CO/sub 2/F followed by hydrolysis give 2-FDG and 2-FDM. The ratio of 2-FDG to 2-FDM depends largely on the polarity of the solvent rather than on the size of the substituents on the hydroxyl groups. The amount of 2-FDM in the final product from the reaction of 1B-D glucal with CH/sub 3/CO/sub 2/F ranges from 4% in non-polar solvents (Freon-11, CCl/sub 4/, hexane) to --20% in polar solvents (HOAc, CH/sub 3/OH, DMF, acetone). Therefore, the reaction of CH/sub 3/CO/sub 2/F with glucal in Freon-11 or other non-polar solvents would be the method of choice for the synthesis of 2-/sup 18/FDG.

• Research Organization: Brookhaven National Lab., Upton, NY
• OSTI ID: 7030712
• 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
ANTIMETABOLITES
BETA DECAY RADIOISOTOPES
BETA-PLUS DECAY RADIOISOTOPES
BY-PRODUCTS
CHEMICAL COMPOSITION
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHEMISTRY
DECOMPOSITION
DRUGS
FLUORINE 18
FLUORINE ISOTOPES
FLUORODEOXYGLUCOSE
FREONS
HALOGENATED ALIPHATIC HYDROCARBONS
HOURS LIVING RADIOISOTOPES
HYDROLYSIS
HYDROXYL RADICALS
IMPURITIES
ISOTOPES
KINETICS
LABELLED COMPOUNDS
LABELLING
LIGHT NUCLEI
LYSIS
NUCLEI
ODD-ODD NUCLEI
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
PURIFICATION
RADIATION CHEMISTRY
RADICALS
RADIOISOTOPES
RADIOPHARMACEUTICALS
REACTION KINETICS
SOLVOLYSIS
STEREOCHEMISTRY
SYNTHESIS
YIELDS