One-Pot Azidochlorination of Glycals
One-Pot Azidochlorination of Glycals
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DOI：
10.1021/ol102750h
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发表时间：
2011-02-18
期刊：
影响因子：
5.2
通讯作者：
Sewald, Norbert
中科院分区：
文献类型：
--
作者：
Plattner, Carolin;Hoefener, Michael;Sewald, Norbert
一个简单的一锅叠氮氯化制备含氮的Kwoenigs-Knorr糖基供体的反应进行保护的糖与叠氮化钠，氯化铁，和过氧化氢。不同的单糖和二糖半乳糖醛和葡糖醛以高度α-选择性的方式转化为2-叠氮基糖基氯化物。从二糖半乳糖醛酸开始，以直接的方式获得用于合成T抗原的结构单元。反应条件的简单性允许2-叠氮基取代的糖基氯化物的有效且可扩展的α-选择性合成。
A simple one-pot azidochlorination for the preparation of nitrogen-containing Kwoenigs-Knorr glycosyl donors proceeds upon reaction of protected glycals with sodium azide, ferric chloride, and hydrogen peroxide. Different mono- and disaccharide galactals and glucals are converted in a highly alpha-selective manner to the 2-azido glycosyl chlorides. Starting from disaccharide galactals, building blocks for the synthesis of the T-antigen are obtained in a straightforward manner. The simplicity of the reaction conditions allows for an efficient and scalable alpha-selective synthesis of 2-azido substituted glycosyl chlorides.