標題: Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
作者: Chao, Chin-Sheng
Chen, Min-Chun
Lin, Shih-Che
Mong, Kwok-Kong T.
應用化學系
Department of Applied Chemistry
關鍵字: p-toluenesulfonic acid;acid-catalyzed acetylation;amino sugars;one-pot protecting group manipulation
公開日期: 7-Apr-2008
摘要: Inexpensive and readily available sulfonic acids, p-toluenesulfonic acid, and sulfuric acid are versatile and efficient catalysts for the peracetylation of a broad spectrum of carbohydrate substrates in good yield and in a practical time frame. Three appealing features in sulfonic acid-catalyzed acetylation of free sugars were explored including (1) suppression of furanosyl acetate formation for D-galactose and L-fucose; (2) high yielding chemoselective acetylation of sialic acid under appropriate conditions; and (3) peracetylation of amino sugars with different amino protecting functions. Simple one-pot two step acetylation-thioglycosidation methods for the expeditious synthesis of p-tolyl per-O-acetyl thioglycosides were also delineated. (C) 2008 Elsevier Ltd. All rights reserved.
URI: http://dx.doi.org/10.1016/j.carres.2008.01.014
http://hdl.handle.net/11536/9469
ISSN: 0008-6215
DOI: 10.1016/j.carres.2008.01.014
期刊: CARBOHYDRATE RESEARCH
Volume: 343
Issue: 5
起始頁: 957
結束頁: 964
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