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Lipopolysaccharides 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. [ABSTRACT FROM AUTHOR]

A total synthesis of nonasaccharide repeating units and shorter sequences from Phellinus ribis glycans with strong immunostimulating activities was achieved by an orthogonal one-pot glycosylation strategy based on an N -phenyltrifluoroacetimidate glycosylation, a Yu glycosylation, and an ortho -(1-phenylvinyl)benzoate glycosylation. The issues inherent to thioglycosides-based orthogonal one-pot glycosylations, such as aglycone transfer, are eliminated by this one-pot glycosylation strategy, which streamlines the chemical synthesis of glycans. [ABSTRACT FROM AUTHOR]

Inside Cover: Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One-Pot Glycosylation Strategy (Angew. Keywords: Anti-Inflammatory Activity; Lipopolysaccharides; Oligosaccharide Synthesis; Orthogonal One-Pot Glycosylation; Stereoselectivity EN Anti-Inflammatory Activity Lipopolysaccharides Oligosaccharide Synthesis Orthogonal One-Pot Glycosylation Stereoselectivity 1 1 1 05/16/23 20230522 NES 230522 B Lipopolysaccharides b from I Bacteroides vulgatus i represent interesting targets for the treatment of inflammatory bowel diseases. Anti-Inflammatory Activity, Lipopolysaccharides, Oligosaccharide Synthesis, Orthogonal One-Pot Glycosylation, Stereoselectivity. [Extracted from the article]

In their Research Article (e202301351), Guozhi Xiao and co-workers accomplished the first synthesis of a tridecasaccharide motif from I Bacteroides vulgatus i lipopolysaccharides by a strategy involving orthogonal one-pot glycosylation reactions based on glycosyl I ortho i -(1-phenylvinyl)benzoates, which avoided issues such as aglycone transfer and the unpleasant odor of thioglycoside-based orthogonal one-pot glycosylation. Anti-Inflammatory Activity, Lipopolysaccharides, Oligosaccharide Synthesis, Orthogonal One-Pot Glycosylation, Stereoselectivity Keywords: Anti-Inflammatory Activity; Lipopolysaccharides; Oligosaccharide Synthesis; Orthogonal One-Pot Glycosylation; Stereoselectivity EN Anti-Inflammatory Activity Lipopolysaccharides Oligosaccharide Synthesis Orthogonal One-Pot Glycosylation Stereoselectivity 1 1 1 05/16/23 20230522 NES 230522 B Lipopolysaccharides b from I Bacteroides vulgatus i represent interesting targets for the treatment of inflammatory bowel diseases. [Extracted from the article]