An Organocatalytic Regioselective Acylation of Carbohydrates: Toward the Development of Intelligent Catalysts

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A catalytic one-step procedure for the chemo- and regioselective acylation of carbohydrates has been developed. With 1 mol% of an organocatalyst, acylation of octyl β-D-glucopyranoside took place preferentially on the secondary hydroxyl group at C (4) among four hydroxyl groups including the primary hydroxyl group at C (6) in 99% selectivity and in 98% yield. Competitive acylation between primary and secondary hydroxyl groups usually takes place chemoselectively at the primary one. On the other hand, with the present catalyst, chemoselective acylation in favor of a secondary hydroxyl group and regioselective acylation in favor of one out of three secondary hydroxyl groups can be performed with perfect selectivity.