ChemInform Abstract: Hydrolysis of the GlcNAc Oxazoline: Deamidation and Acyl Rearrangement.
Abstract
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ChemInform Abstract
The specific deamidation of compound (I) under acidic conditions affords the p-toluenesulfonate (III), which undergoes base-catalyzed O- 1 → N-2 acyl rearrangement to give the 2-acetamido derivative ( III). Hydrolysis experiments of (I) show that the amino ester (II) represents the kinetic product, while amido alcohol (III) is the thermodynamic product. Acylation of (II) offers the route to novel glycoconjugates such as (V).
