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A catalytic method is developed for the diastereoselective acylation of the anomeric hydroxyl group in diverse carbohydrates to form either alpha- or beta-anomeric esters. While exclusive formation of the beta-isomer was observed in most sugar substrates with one enantiomer of the chiral catalyst, moderate to high alpha-selectivity was obtained by using the other enantiomer of the chiral catalyst. The resulting alpha- and beta-anomeric esters have very different reactivity toward a reduction reaction.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics