Rhodium- and copper-catalyzed amidoglycosylation reactions of glycal 3-carbamates provide synthetic access to stereochemically varied 2-amino sugar derivatives that contain a cis-fused 2<i>N</i>,3<i>O</i>-oxazolidinone moiety. Functionality for further chemoselective elaboration, including azido and alkynyl groups, can also be incorporporated within the 2-amino sugar products. Additionally, the corresponding free reducing sugars are readily accessible from the initial amidoglycosylation products. Using this synthetic methodology, we have prepared a range of 2-amino sugars for glycodiversification studies and are exploring their utility in coupling reactions with aglycons.

Synthesis of 2-amino sugar building blocks and application for glycodiversification studies

249th National Meeting (2015)

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