Showing papers on "Glucal published in 1985"
TL;DR: In this article, a TLC-system was developed to separate FDG and FDM on monosodium-phosphate impregnated silica plates, and the resulting FDG (2-deoxy-2-fluoro-tetra-O-acetyl-D -glucose) was contaminated with 15-20% of the corresponding mannose derivative.
43 citations
24 citations
Journal Article•
TL;DR: The steric effects and solvent effects on the stereoselectivity of the reactions of glycals with CH/sub 3/CO/sub 2/F have been investigated in this article, showing that 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.
Abstract: 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.
11 citations