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

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.

SUBMITTER: Hettiarachchi IL

PROVIDER: S-EPMC9389860 | biostudies-literature | 2021 Dec

REPOSITORIES: biostudies-literature

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

Hettiarachchi Ishani Lakshika IL Meng Shuai S Chahine Mira M Li Xiaohua X Zhu Jianglong J

European journal of organic chemistry 20211112 48

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. ...[more]

PMID: 35990817

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