173465-71-9Relevant academic research and scientific papers
Synthetic route for 14C-labeling of a bioactive lipid A analogue
Fukase,Aoki,Kinoshita,Suda,Kurosawa,Zahringer,Rietschel,Kusumoto
, p. 8645 - 8648 (2007/10/02)
A synthetic route for 14C-labeling of a phosphonooxyethyl (PE) analogue of E. coli lipid A was established by cold experiments. The PE analogue is chemically more stable than natural lipid A but shows particularly identical biological activity. The glycosidation of ethylene glycol unit as the 14C-labeled position was effected with a disaccharide thioglycoside by use of a hypervalent iodine reagent, PhIO-SnClO4-AgClO4, as an activator. p-Methoxybenzyl group used for the protection of the distal hydroxyl group of ethylene glycol was selectively removed by trimethylsilyl triflate in CH3CN-CH2Cl2 followed by phosphorylation and deprotection gave the target compound.
