Stereoselective β-Mannosylation via Anomeric O-Alkylation with L-Sugar-Derived Electrophiles

Ishani Lakshika Hettiarachchi; Shuai Meng; Mira Chahine; Xiaohua Li; Jianglong Zhu

doi:10.1002/ejoc.202100903

Stereoselective β-Mannosylation via Anomeric O-Alkylation with L-Sugar-Derived Electrophiles

European J Org Chem. 2021 Dec 28;2021(48):6682-6687. doi: 10.1002/ejoc.202100903. Epub 2021 Nov 12.

Authors

Ishani Lakshika Hettiarachchi¹, Shuai Meng¹, Mira Chahine², Xiaohua Li², Jianglong Zhu¹

Affiliations

¹ Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States. https://www.utoledo.edu/nsm/chemistry/people/Webpages/Zhu.html.
² Department of Natural Sciences, University of Michigan-Dearborn, 4901 Evergreen Road, Dearborn, Michigan 48128, United States.

Abstract

A total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O-antigen is reported. This synthesis features a key β-mannosylation reaction via cesium carbonate-mediated anomeric O-alkylation of a partially protected D-mannose with an L-fucose-derived electrophile for the first time.

Keywords: Anomeric O-Alkylation; Carbohydrates; Glycosylation; Microbial Glycans; β-Mannosylation.

Grants and funding

U01 GM125289/GM/NIGMS NIH HHS/United States