Selective Anomeric Acetylation of Unprotected Sugars with Acetic Anhydride in Water
Xin Qiu, Daniel Chong, Antony J. Fairbanks
Abstract
Unprotected sugars are selectively acetylated simply by stirring in aqueous solution in the presence of acetic anhydride and a weak base such as sodium carbonate. The reaction is selective for acetylation of the anomeric hydroxyl group of mannose, 2-acetamido, and 2-deoxy sugars and can be performed on a large scale. Competitive intramolecular migration of the 1- O -acetate to the 2-hydroxyl group when these two substituents are cis causes over-reaction and the formation of product mixtures.
Topics & Concepts
ChemistryAnomerAcetic anhydrideAcetylationAqueous solutionOrganic chemistryIntramolecular forceMannoseSodium carbonateSodium acetateMedicinal chemistrySodiumCatalysisBiochemistryGeneCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchEnzyme Catalysis and Immobilization