Affiliation:
1. State Key Laboratory of Phytochemistry and Plant Resources in West China Kunming Institute of Botany University of Chinese Academy of Sciences Chinese Academy of Sciences 132 Lanhei Road Kunming 650201 China
2. Department of Chemistry Kunming University 2 Puxing Road Kunming 650214 China
Abstract
AbstractLipopolysaccharides from Bacteroides vulgatus represent interesting targets for the treatment of inflammatory bowel diseases. However, efficient access to long, branched and complex lipopolysaccharides remains challenging. Herein, we report the modular synthesis of a tridecasaccharide from Bacteroides vulgates through an orthogonal one‐pot glycosylation strategy based on glycosyl ortho‐(1‐phenylvinyl)benzoates, which avoids the issues of thioglycoside‐based one‐pot synthesis. Our approach also features: 1) 5,7‐O‐di‐tert‐butylsilylene‐directed glycosylation for stereoselective construction of the α‐Kdo linkage; 2) hydrogen‐bond‐mediated aglycone delivery for the stereoselective formation of β‐mannosidic bonds; 3) remote anchimeric assistance for stereoselective assembly of the α‐fucosyl linkage; 4) several orthogonal one‐pot synthetic steps and strategic use of orthogonal protecting groups to streamline oligosaccharide assembly; 5) convergent [1+6+6] one‐pot synthesis of the target.
Funder
State Key Laboratory of Phytochemistry and Plant Resources in West China
Subject
General Chemistry,Catalysis
Cited by
6 articles.
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