Access to Diosgenyl Glycoconjugates via Gold(I)-Catalyzed Etherification of Diosgen-3-yl ortho-Hexynylbenzoate

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• 作者：Li Zhang ; Linfeng Li ; Shujin Bai ; Xin Zhou ; Peng Wang ; Ming Li
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：18
• 期：23
• 页码：6030-6033
• 全文大小：399K
• ISSN：1523-7052

文摘

An efficient protocol for the synthesis of diverse diosgen-3-yl glycoconjugates, a class of novel synthetic analogs of natural saponins of biological significance, has been developed. The method relies on gold(I)-catalyzed etherification of diosgen-3-yl ortho-hexynylbenzoate with stoichiometric sugar alcohols to afford the corresponding glycoconjugates in 38%–99% yields. The reaction involves the preferential attack of hydroxyl groups to the C3 position of homoallylic carbocation intermediate and displays a broad substrate scope and a good functional group tolerance.