title: Strained olefin enables triflic anhydride mediated direct dehydrative glycosylation.
abstract: For the first time, we demonstrated that Tf2O mediated direct dehydrative glycosylation was possible simply with strained olefins, and other typical bases were inhibitors of this reaction. We optimized the glycosylation conditions and found that typical benzyl protected 1-OH pyranosyl donors and certain alcohol acceptors were suitable for our glycosylation system. Furthermore, we found that complete 1,2-trans selectivity and a wider acceptor scope could be achieved with 2-O-Bz 3,4,6-tri-O-Bn pyranosyl donors.
authors.affiliation: School of Pharmacy, China Pharmaceutical University, 24 Tongjiaxiang, Nanjing 210009, P. R. China.
authors.forename: Guohua
authors.initials: G
authors.lastname: Chen
authors.forename: Qiang
authors.initials: Q
authors.lastname: Yin
authors.forename: Jian
authors.initials: J
authors.lastname: Yin
authors.forename: Xiangying
authors.initials: X
authors.lastname: Gu
authors.forename: Xiao
authors.initials: X
authors.lastname: Liu
authors.forename: Qidong
authors.initials: Q
authors.lastname: You
authors.forename: Yue-Lei
authors.initials: YL
authors.lastname: Chen
authors.forename: Bing
authors.initials: B
authors.lastname: Xiong
authors.forename: Jingkang
authors.initials: J
authors.lastname: Shen
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D005663:Furans / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D013449:Sulfonamides / Q000737:chemistry*
chemical_list: D000475:Alkenes; D005663:Furans; D013449:Sulfonamides; C474725:triflic anhydride