title: Evidence of robust participation by an equatorial 4-O group in glycosylation on a 2-azido-2-deoxy-glucopyranosyl donor.
abstract: Although there are numerous claims of remote group participation leading to the synthesis of the expected glycosides with improved anomeric geometry outcome in glycosylation, there is still a lack of enough strong evidence and this has led to a long-term debate, particularly for equatorial 4-O group participation. In this work, we were able to synthesize and isolate a stable seven-membered trichlorooxazepine ring bridging intermediate with a high yield by employing a 2-azido-2-deoxy-glucopyranosyl donor, which provides strong evidence to support the putative participation of the equatorial 4-O group in glycosylation.
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, China. dingning@fudan.edu.cn and School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China.
authors.forename: Dongming
authors.initials: D
authors.lastname: Yao
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, China. dingning@fudan.edu.cn.
authors.forename: Yichu
authors.initials: Y
authors.lastname: Liu
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, China. dingning@fudan.edu.cn.
authors.forename: Shiqiang
authors.initials: S
authors.lastname: Yan
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, China. dingning@fudan.edu.cn.
authors.forename: Yingxia
authors.initials: Y
authors.lastname: Li
authors.affiliation: School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China.
authors.forename: Chun
authors.initials: C
authors.lastname: Hu
authors.affiliation: Department of Medicinal Chemistry, School of Pharmacy, Fudan University, Shanghai, 201203, China. dingning@fudan.edu.cn.
authors.forename: Ning
authors.identifier: http://orcid.org/0000-0002-6797-8797
authors.initials: N
authors.lastname: Ding