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Amine-Induced Deacylation of Carbohydrate Derivatives Under Anhydrous Conditions

1993; Taylor & Francis; Volume: 12; Issue: 1 Linguagem: Inglês

10.1080/07328309308018537

1532-2327

Oscar Moradei, Silvana Leit, Cecile du Mortier, Alicia Fernández Cirelli, Joachim Thiem,

Chemical Synthesis and Analysis

Abstract Methanolysis of acylated carbohydrate derivatives was effectively performed using tertiary amines in the absence of water at room temperature. The reaction was performed with acetylated and benzoylated alditols, aldoses, lactones, orthoesters, glycosides, and disaccharides. N-methyl-pyrrolidine proved to be especially suitable for synthetic purposes and deacylated compounds were obtained in excellent yields. The mild conditions employed and the minimum work-up needed make this method appropriate for the deacylation of labile compounds.