A Stereoselective Glycosylation Approach to the Construction of 1,2-trans-β-d-Glycosidic Linkages and Convergent Synthesis of Saponins,Chemistry - A European Journal

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A Stereoselective Glycosylation Approach to the Construction of 1,2-trans-β-d-Glycosidic Linkages and Convergent Synthesis of Saponins
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2021-12-03 , DOI: 10.1002/chem.202104002
Fuzhu Yang _{1,

2} , Wu Hou ₁ , Dapeng Zhu ₃ , Yu Tang ₃ , Biao Yu _{2,

3}

Affiliation

Direct action: A highly stereoselective glycosylation protocol for the synthesis of 1,2-trans-β-d- or α-l-glycosidic linkages is disclosed, which employs a combination of glycosyl N-phenyltrifluroacetimidates as donors, FeCl₃ as promoter, and CH₂Cl₂/nitrile as solvent and exploits glycosidation via glycosyl α-nitrilium intermediates. A variety of natural saponins containing (1→2)-linked glycan motifs are thus synthesized in convergent manner by direct glycosylation with (1→2)-linked glycan donors.

中文翻译：

构建 1,2-反式-β-d-糖苷键和聚合合成皂苷的立体选择性糖基化方法

直接作用：公开了一种用于合成 1,2-反式-β- d-或 α -l-糖苷键的高度立体选择性糖基化方案，该方案采用糖基N-苯基三氟乙酰亚胺酯作为供体、FeCl ₃作为促进剂和CH ₂ Cl ₂ /腈作为溶剂，通过糖基 α-腈中间体进行糖苷化。因此，通过与 (1→2)-连接的聚糖供体直接糖基化，以收敛的方式合成了多种含有 (1→2)-连接的聚糖基序的天然皂苷。

更新日期：2022-02-01

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