Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

Jon K. Fairweather, Ligong Liu, Tomislav Karoli, Vito Ferro
2012 Molecules  
A 6-deoxy--L-talopyranoside acceptor was readily prepared from methyl -L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired -linked disaccharide (69-90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (: = 6:1), but the desired -linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate
more » ... nding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.
doi:10.3390/molecules17089790 pmid:22895025 fatcat:sqca5y77dzay5le2ohlzmp6wza