Showing papers on "Glucal published in 1984"

Fluorination in aqueous media with elemental fluorine: The synthesis of (F-18)2-FDG

Abstract: Continued emphasis on the use of F-18 labeled 2-deoxy-2-fluor-D-glucose (2-FDG) for the determination of local organ glucose metabolism in normal and diseased states with PET provides the impetus for investigation of more facile procedures for synthesizing this important radiopharmaceutical. The authors report herein the regio- and stereo-selective addition of fluorine across a double bond, i.e. D-glucal (1), in aqueous media to yield 2-FDG. 2-FDG was prepared by bubbling 0.2% fluorine in neon into an aqueous solution containing an equimolar amount of glucal at room temperature. Hydrolysis of the resultant fluorinated product mixture with 1 N HCL (120/sup 0/C, 15m) followed by chromatographic purification, using an ion retardation resin-alumina column gave 2-FDG in about 60% yield. The final product was identified by TLC, /sup 19/F NMR (94.1 MHz, deuterium oxide, hexafluorobezene (external standard) delta + 32.81 ppm (..cap alpha..-anomer, 48.5%) and + 32.51 ppm (..beta..-anomer, 51.5%)), and by its conversion to the corresponding 6-phosphate with yeast hexokinase as shown by HPLC. This method was extended to the synthesis of (F-18)2-FDG. (F-18)2-FDG was similarly prepared as described above from (F-18)fluorine in radiochemical yields of 25-30% (50-60% of theoretical maximum) with a processing time of 30 min after EOB. This synthesis of (F-18)2-FDGmore » provides simplification, reduced processing time, and a radiochemical yield that is competitive with other methods recently described.« less