Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
Versatile acetylation of carbohydrate substrates with bench-top sulfonic acids and application to one-pot syntheses of peracetylated thioglycosides
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DOI：
10.1016/j.carres.2008.01.014
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发表时间：
2008-04-07
影响因子：
3.1
通讯作者：
Mong, Kwok-Kong T.
中科院分区：
文献类型：
--
作者：
Chao, Chin-Sheng;Chen, Min-Chun;Mong, Kwok-Kong T.
廉价且容易获得的磺酸、对甲苯磺酸和硫酸是通用且高效的催化剂，可在可行的时间内以良好的收率对多种碳水化合物底物进行全乙酰化。探索了磺酸催化游离糖乙酰化的三个吸引人的特征，包括（1）抑制 D-半乳糖和 L-岩藻糖的乙酸呋喃糖酯形成； (2)在适当的条件下对唾液酸进行高产率的化学选择性乙酰化； (3)具有不同氨基保护功能的氨基糖的全乙酰化。还描述了快速合成对甲苯基过-O-乙酰基硫代糖苷的简单的一锅两步乙酰化-硫代糖苷化方法。 (C) 2008 Elsevier Ltd. 保留所有权利。
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.