125474-13-7Relevant academic research and scientific papers
Synthesis of urine drug metabolites: Glucuronosyl esters of carboxymefloquine, indoprofen, (S)-naproxen, and desmethyl (S)-naproxen
Lahmann, Martina,Bergstroem, Moa,Turek, Dominika,Oscarson, Stefan
, p. 123 - 132 (2007/10/03)
A general procedure for the synthesis of 1-O-acyl-β-D-glucuronic acids using the benzyl 1-O-trichloroacetimidoyl-2,3,4-tri-O-benzyl-D- glucopyranuronate 6 as donor is exemplified by the synthesis of the urine metabolites of (S)-naproxen, desmethyl (S)-naproxen, indoprofen, and carboxymefloquine. The key intermediate benzyl 2,3,4-tri-O-benzyl-D- glucopyranuronate 5 is easily accessible in four steps (29%) from the peracetylated β-D-glucuronic acid 1. Copyright
Synthesis of bile acid 24-acyl glucuronides
Goto, Junichi,Murao, Naoaki,Oohashi, Junji,Ikegawa, Shigeo
, p. 180 - 185 (2007/10/03)
The synthesis of acyl glucuronides of common bile acids is described. By means of the Mitsunobu reaction employing diethylazodicarboxylate and triphenylphosphine, bile acids were condensed through the inherent C-24 carboxy group with benzyl 2,3,4-tri-O-benzyl-D-glucopyranuronate, which was prepared from 1-O-methyl-α-D-glucose. The separation and purification of the β2-anomers at the anomeric position of the sugar moiety were attained by preparative thin-layer chromatography and/or high-performance liquid chromatography on a column packed with phenyl-bonded silica using H2O-MeOH as a mobile phase. The removal of the benyl group on the sugar moiety was achieved by catalytic hydrogenation with 10% palladium on carbon to yield the desired acyl glucuronides of bile acids. The structures of these acyl glucuronides were confirmed by proton nuclear magnetic resonance spectral properties.
