title: Access to Diosgenyl Glycoconjugates via Gold(I)-Catalyzed Etherification of Diosgen-3-yl ortho-Hexynylbenzoate.
abstract: 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.
authors.affiliation: Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao, Shandong 266003, P. R. China.
authors.forename: Li
authors.initials: L
authors.lastname: Zhang
authors.affiliation: Department of Pharmaceutical Sciences, Skaggs School of Pharmacy and Pharmaceutical Sciences, University of Colorda Anschutz Medical Campus , Aurora, Colorado 80045, United States.
authors.forename: Linfeng
authors.initials: L
authors.lastname: Li
authors.affiliation: Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao, Shandong 266003, P. R. China.
authors.forename: Shujin
authors.initials: S
authors.lastname: Bai
authors.affiliation: Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao, Shandong 266003, P. R. China.
authors.forename: Xin
authors.initials: X
authors.lastname: Zhou
authors.affiliation: Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao, Shandong 266003, P. R. China.
authors.forename: Peng
authors.initials: P
authors.lastname: Wang
authors.affiliation: Key Laboratory of Marine Medicine, Chinese Ministry of Education, School of Medicine and Pharmacy, Ocean University of China , Qingdao, Shandong 266003, P. R. China.
authors.forename: Ming
authors.initials: M
authors.lastname: Li