邻苯二甲醇唾液酸单酯的合成及分子内糖基化反应。供体构型和氮保护基对环化产率和选择性的重要性；一种表明乙腈参与反应的N-唾液酰乙酰胺的分离与表征
Synthesis and intramolecular glycosylation of sialyl mono-esters of o-xylylene glycol. The importance of donor configuration and nitrogen protecting groups on cyclization yield and selectivity; isolation and characterization of a N-sialyl acetamide indicative of participation by acetonitrile.
作者信息
Amarasekara Harsha, Crich David
机构信息
Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.
Department of Chemistry, Wayne State University, Detroit, MI 48202, USA.
出版信息
Carbohydr Res. 2016 Nov 29;435:113-120. doi: 10.1016/j.carres.2016.09.019. Epub 2016 Oct 8.
Abstract
The synthesis and cyclization reactions, leading to spirocyclic medium ring-sized diolides, of o-(hydroxymethyl)xylylene monoesters of sialyl thioglycosides is described. Cyclization yields and stereoselectivities are found to vary as a function of the anomeric stereochemistry of the thioglycoside and of the N5 protecting group, and these effects are discussed in terms of the reaction mechanism. Cyclization in the presence of acetonitrile results in the isolation and characterization of a Ritter-type N-sialyl acetamide, which affords strong evidence for the participation of acetonitrile in the form of sialyl nitrilium ions.
摘要
描述了唾液酸硫代糖苷的邻（羟甲基）亚二甲苯基单酯合成并环化生成螺环中环大小的二内酯的反应。发现环化产率和立体选择性随硫代糖苷的异头立体化学和N5保护基的变化而变化，并根据反应机理讨论了这些影响。在乙腈存在下进行环化反应，得到并表征了一种里特型N-唾液酰乙酰胺，这为乙腈以唾液酰腈离子的形式参与反应提供了有力证据。
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