Abstract
The synthesis of 2-acylamino-2-deoxysugars 1,2- trans-glycosides is described via the oxazolinium salt generated from an O,N-acetylated 1,2- cis-glycosyl halide of 2-amino-2-deoxysugar under the conditions of halide-anion catalysis. This salt was then interacted with alcohol to form the corresponding 1,2- trans-glycoside. A method for removing the generated hydrogen chloride is described. The conditions of this synthesis allow glycosides with acid-labile functional groups to be obtained. Suppression of the anomerisation of 1,2- trans-glycosides was achieved by the introduction of N,N′-dicyclohexyl urea into the reaction medium.
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