Highly Stereoselective 1,2- cis -Glycosylation with 2-Azidofucosyl Donors: Access to the Pentasaccharide Motif from Escherichia coli O4:K6
Abstract
Highly stereoselective 1,2- cis -glycosylation with 2-azidofucosyl donors has been developed, which has a broad substrate scope including strong and weak alcoholic acceptors, carboxylic acids, bioactive and complex natural products and drugs, mild conditions, and excellent yields and stereoselectivities. This method has been successfully applied to the first chemical synthesis of O -antigen pentasacccharide repeating unit from Escherichia coli O4:K6, which also features the following steps: 1) DMF-modulated glycosylation for highly stereoselective assembly of two 1,2- cis -glucosidic linkages; and 2) one-pot assembly of 1,2- trans - and 1,2- cis -glycosidic linkages.
Fields of Study & Subjects
Carbohydrate Chemistry and Synthesis
Microbial Natural Products and Biosynthesis
Click Chemistry and Applications
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 5
- Pages
- 1882–1886
- Publication date
- 23 January 2026
- Language
- EN