2,4-Dinitrobenzenesulfonamide-Directed S(N)2-Type Displacement Reaction Enables Synthesis of beta-D-Glycosaminosides
2,4-Dinitrobenzenesulfonamide-Directed S(N)2-Type Displacement Reaction Enables Synthesis of beta-D-Glycosaminosides
复制标题
2,4-二硝基苯磺酰胺导向的 S(N)2 型置换反应可合成 β-D-氨基糖苷
DOI：
10.1021/acs.orglett.9b00688
复制
发表时间：
2019
期刊：
影响因子：
5.2
通讯作者：
Li Ming
中科院分区：
文献类型：
--
作者：
Wang Xianyang;Wang Peng;Li Dongwei;Li Ming
建立了一种有效的构建β-d-葡萄糖/半乳糖氨基糖键的方法，该方法利用非参与的强吸电子C-2- 2，4-二硝基苯磺酰胺（DNsNH）指导的糖基邻己炔基苯甲酸酯的类SN 2糖基化反应。该反应适用于广泛的O-、N-和C-亲核试剂，并具有在温和条件下以高产率方便地将DNsNH转化为AcNH的特点。合成了β-d-（1→3）-氨基葡萄糖三糖，为合成脑膜炎奈瑟菌荚膜多糖相关寡糖奠定了基础。
An efficient protocol to construct β-d-gluco-/galactosaminosyl linkages was established using nonparticipating and strong electron-withdrawing C-2-2,4-dinitrobenzenesulfonamide (DNsNH)-directed SN2-like glycosylation of glycosylortho-hexynylbenzoates. The reaction is applicable to a wide range of O-, N-, and C-nucleophiles and features convenient conversion of DNsNH into AcNH in high yield under mild conditions. Oligomerization-ready trisaccharide, composed of β-d-(1→3)-glucosamino residues, has been achieved, setting a solid foundation for the synthesis of oligosaccharides associated withNeisseria meningitidiscapsular polysaccharide.