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Synthesis of alpha- and beta-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling

, : Synthesis of alpha- and beta-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling. Journal of Organic Chemistry 67(13): 4475-4486

A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge.


PMID: 12076144

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