527738-82-5Relevant academic research and scientific papers
Indium-mediated stereoselective synthesis of truncated, 6- and 7-carbon sialic acids
Warwel, Mathias,Fessner, Wolf-Dieter
, p. 2104 - 2106 (2002)
Several 6- and 7-carbon sialic acid derivatives were synthesized, without tedious protecting group manipulations, in high overall yields. A key step of the synthesis was the chain extension of suitable α-amino aldehyde derivatives by an indium-mediated addition of ethyl 2-(bromomethyl)acrylate. Under acidic reaction conditions, the corresponding extended enoates were obtained with high trans-stereoselectivity. Ozonolysis furnished the desired 4-acylamino-substituted hexulosonic and heptulosonic acids in free form for biochemical studies.
