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

• DOI: 10.1021/acs.orglett.6b02963
• Publication Date: 2016-11-16T20:56:19Z
• Authors: Li Zhang; Linfeng Li; Shujin Bai; Xin Zhou; Peng Wang; Ming Li
• Keywords: Glycoconjugate

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