Thioglycuronides:: Synthesis and application in the assembly of acidic oligosaccharides

被引:137
|
作者
van den Bos, LJ [1 ]
Codée, JDC [1 ]
van der Toorn, JC [1 ]
Boltje, TJ [1 ]
van Boom, JH [1 ]
Overkleeft, HS [1 ]
van der Marel, GA [1 ]
机构
[1] Leiden Univ, Leiden Inst Chem, NL-2300 RA Leiden, Netherlands
关键词
D O I
10.1021/ol049380+
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.
引用
收藏
页码:2165 / 2168
页数:4
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