title: Direct glycosylation of bioactive small molecules with glycosyl iodide and strained olefin as acid scavenger.
abstract: A new strategy for diversity-oriented direct glycosylation of bioactive small molecules was developed. This reaction features (−)-β-pinene as acid scavenger and work with glycosyl iodides under mild conditions. With the aid of RP-HPLC and chiral SFC separation techniques, the new direct glycosylation proved effective at gram scale on bioactive small molecules including AZD6244, podophyllotoxin, paclitaxel, and docetaxel. Interesting glycoside derivatives were efficiently created with good yields and 1,2-cis selectivity.
authors.forename: Xiangying
authors.initials: X
authors.lastname: Gu
authors.forename: Lin
authors.initials: L
authors.lastname: Chen
authors.forename: Xin
authors.initials: X
authors.lastname: Wang
authors.forename: Xiao
authors.initials: X
authors.lastname: Liu
authors.forename: Qidong
authors.initials: Q
authors.lastname: You
authors.forename: Wenwei
authors.initials: W
authors.lastname: Xi
authors.forename: Li
authors.initials: L
authors.lastname: Gao
authors.forename: Guohua
authors.initials: G
authors.lastname: Chen
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*; D001562:Benzimidazoles / Q000737:chemistry*; D000077143:Docetaxel; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D007454:Iodides / Q000737:chemistry*; D017239:Paclitaxel / Q000737:chemistry*; D013237:Stereoisomerism; D043823:Taxoids / Q000737:chemistry*
chemical_list: C517975:AZD 6244; D000475:Alkenes; D001562:Benzimidazoles; D006027:Glycosides; D007454:Iodides; D043823:Taxoids; D000077143:Docetaxel; D017239:Paclitaxel