Oligosaccharide chains are susceptible to chemical and enzymatic hydrolysis.  Therefore, replacement of glycosidic linkage with a more robust functionality, such as urea, is an enticing prospect in the field of aminoglucoside antibiotics.  There are few reported methods for the selective formation of glycosyl ureas, with minimal report of a-selective syntheses in particular.  We have developed a new method for the stereoselective synthesis of a-glycosyl urea, where a cationic Ni(II) species mediates the selective [1,3]-rearrangement from a-glycosyl trichloroacetimidate to a-trichloroacetamide. The resultant acetamide is directly converted to the corresponding glycosyl urea.

Nickel (II) catalyzed stereoselective synthesis of α-glycosyl urea

244th National Meeting (2012)

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