We have developed a synthesis of oxazolidinone derivatives of 2-amino free-reducing sugars that begins with a metallanitrene-mediated amidoglycosylation reaction of glycal 3-carbamates to install a 2N,3O-oxazolidinone and incorporate a cleavable anomeric group. By using glycal substrates with varying stereochemistry at the C3 and C4 positions, we have generated a stereodiverse set of 2-amino sugar building blocks. Further structural variety has been achieved by inclusion of an azido group at the C6 position and by copper-induced cross-coupling for N-arylation of the oxazolidinone. Subsequent deprotection of the anomeric center gives structurally diverse free-reducing sugars needed for neoglycosylation via a one-step coupling reaction with core structures bearing a secondary alkoxyamine linker. Conditions for this condensation are currently being optimized for the C6- and N-functionalized oxazolidinone sugars.

Metal-mediated synthesis of 2-amino free-reducing sugars as glycodiversification building blocks

255th National Meeting (2018)

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