卤间化合物（ICl/IBr）与三氟甲磺酸银在硫代糖苷活化中的应用；神经节苷脂GD3双内酰胺类似物的合成。

Interhalogens (ICl/IBr) and AgOTf in thioglycoside activation; synthesis of bislactam analogues of ganglioside GD3.

作者信息

Meijer Andréas, Ellervik Ulf

机构信息

Organic and Bioorganic Chemistry, Center for Chemistry and Chemical Engineering, Lund University, P.O. Box 124, SE-221 00 Lund, Sweden.

出版信息

J Org Chem. 2004 Sep 17;69(19):6249-56. doi: 10.1021/jo049184g.

DOI:10.1021/jo049184g

PMID:15357583

Abstract

The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 93%, 59%, 40%, and 44% yield, using IBr/AgOTf. The choice of interhalogen (IX) is determined by the donor type used in the glycosylation. We also report some mechanistic investigations leading to further optimization of the IX/AgOTf promoter system.

摘要

新型启动子体系IX/AgOTf（X = Cl或Br）已在两种GD3双内酰胺类似物的合成中得到评估。我们分别使用ICl/AgOTf进行了两次高产率的半乳糖基化反应，产率分别为97%和98%，并使用IBr/AgOTf进行了四次唾液酸化反应，产率分别为93%、59%、40%和44%。卤间化合物（IX）的选择取决于糖基化中使用的供体类型。我们还报告了一些机理研究，这些研究有助于进一步优化IX/AgOTf启动子体系。