14273-88-2Relevant articles and documents
Efficient Synthesis of ω-[18F]Fluoroaliphatic Carboxylic Esters and Acids for Positron Emission Tomography
Belousov, Mikhail V.,Larkina, Mariia S.,Ozerskaya, Anastasia V.,Podrezova, Ekaterina V.,Tolmachev, Vladimir,Yusubov, Mekhman S.,Zhdankin, Viktor V.
, p. 6375 - 6381 (2020/10/20)
[18F]Fluoroaliphatic carboxylic acids are important PET tracers that have demonstrated a considerable potential to address the fatty acid oxidation-dependent processes in clinical patients. Herein, we report an efficient radiosynthetic approach to ω-[18F]fluoroaliphatic carboxylic esters and acids by nucleophilic radiofluorination of the readily available iodocarboxylic esters. Methyl 6-[18F]fluorohexanoate was further applied as a starting material for the preparation of the succinimide ester (NHS ester)-containing bifunctional radiofluorinated prosthetic group in two simple steps, 10 min each. The synthesized NHS ester of 6-[18F]fluorohexanoic acid can serve as an important reagent for a quick and efficient conjugation with peptides or proteins via amino groups of lysines.
SN2 iodide displacement on unsymmetrical cyclic dioxenium salts. A stereoelectronically controlled reaction
Beaulieu, Normand,Deslongchamps, Pierre
, p. 164 - 167 (2007/10/02)
Iodide ion reacts with the cyclic dioxenium salts 1-6 to yield mixtures of iodoester and lactone plus alkyl iodide (Table 1).The formation of iodoester competing with the formation of lactone appears to be an unexpected result.It can, however, be explained by a stereoelectronic effect, similar to the anomeric effect in acetals, which is also responsible for the greater stability of the Z over the E form in dioxenium salts and in esters.
