由 N-糖基二硝基苯磺酰胺合成β-糖基酰胺
Synthesis of β-Glycosyl Amides from N-Glycosyl Dinitrobenzenesulfonamides.
作者信息
Gaitonde Vishwanath, Sucheck Steven J
机构信息
Department of Chemistry and School for Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, USA.
出版信息
J Carbohydr Chem. 2012 Jan 1;31(4-6):353-370. doi: 10.1080/07328303.2012.663431. Epub 2012 Jul 2.
Abstract
The N-glycosyl-2,4-dinitrobenzenesulfonamides were accessed via benzoyl-protected β-glycosyl azides. The azides were reduced with Adams' catalyst to the corresponding amines. The glycosylamines were sulfonated with 2,4-dinitrobenzenesulfonyl chloride to form N-glycosyl-2,4-dinitrobenzenesulfonamides in moderate yields. β-Glycosyl amides were then prepared in 67 - 81 % yields by treatment of the sulfonamides with thioacetic acid and cesium carbonate. The conversion of the glycosylsulfonamide to the glycosyl amide proceeded with high stereoselectivity.
摘要
通过苯甲酰基保护的β-糖基叠氮化物可得到N-糖基-2,4-二硝基苯磺酰胺。叠氮化物用亚当斯催化剂还原为相应的胺。糖基胺用2,4-二硝基苯磺酰氯磺化，以中等产率形成N-糖基-2,4-二硝基苯磺酰胺。然后通过用硫代乙酸和碳酸铯处理磺酰胺，以67 - 81%的产率制备β-糖基酰胺。糖基磺酰胺向糖基酰胺的转化具有高立体选择性。
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