Recent synthetic efforts have demonstrated the ability of indium bromide to catalyze the stereoselective conjugation of beta-N-acetyl glucosamine to alcoholic amino acids in high yield. These glycosylated amino acids were used in solid-phase peptide synthesis for the preparation of site-specifically modified proteins. Given the simplicity and success of this reaction, we wondered if indium bromide could also catalyze the conjugation of beta-N-acetyl glucosamine to other sugars to form disaccharides. Formation of such disaccharides typically require complicated glucosamine donors and dry conditions. Herein, we report the application of indium bromide to the preparation of glucosamine disaccharides at various linkages without the need of complex glucosamine donor sugars and dry conditions.

Application of indium bromide catalyst to the synthesis of disaccharides

255th National Meeting (2018)

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