Additive-assisted synthesis of α-Kdo glycosides with peracetylated glycosyl ynenoate as a donor

A DMF-modulated glycosylation approach for the stereoselective synthesis of α-Kdo glycosides with readily accessible peracetylated Kdo ynenoate as a donor was described. By utilizing this approach, we completed the synthesis of various linkage types of Kdo-Kdo disaccharides and the α-Kdo-containing...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2024-03, Vol.22 (12), p.2365-2369
Main Authors: Miao, He, Lu, Siqian, Chen, Hongyu, Shang, Jintao, Zheng, Jibin, Yang, You
Format: Article
Language:English
Subjects:
Disaccharides
Glycosides
Glycosylation
Lipopolysaccharides
Oligosaccharides
Stereoselectivity
Synthesis
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Summary:A DMF-modulated glycosylation approach for the stereoselective synthesis of α-Kdo glycosides with readily accessible peracetylated Kdo ynenoate as a donor was described. By utilizing this approach, we completed the synthesis of various linkage types of Kdo-Kdo disaccharides and the α-Kdo-containing protected trisaccharide variant relevant to the lipopolysaccharide of Coxiella burnetii strain Nine Mile. Additive-assisted α-selective Kdo glycosylation using a peracetylated Kdo ynenoate is described for stereoselective synthesis of the protected trisaccharide variant relevant to the lipopolysaccharide of Coxiella burnetii strain Nine Mile.
ISSN:1477-0520
1477-0539
DOI:10.1039/d4ob00182f