β-Glycosylations with 2-Deoxy-2-(2,4-dinitrobenzenesulfonyl)-amino-glucosyl/galactosyl Selenoglycosides: Assembly of Partially N-Acetylated β-(1 → 6)-Oligoglucosaminosides

• DOI: 10.1021/acs.joc.3c00725
• Publication Date: 2023-06-12T13:09:19Z
• Authors: Dongwei Li; Jianjun Wang; Xianyang Wang; Zhi Qiao; Lingjun Wang; Peng Wang; Ni Song; Ming Li
• Keywords: Glycoconjugate

An efficient protocol has been established for β-glycosylations with 2-deoxy-2-(2,4-dinitrobenzenesulfonyl)amino (2dDNsNH)-glucopyranosyl/galactopyranosyl selenoglycosides using PhSeCl/AgOTf as an activating system. The reaction features highly β-selective glycosylation a wide range of alcohol acceptors that are either sterically hindered or poorly nucleophilic. Thioglycoside- and selenoglycoside-based alcohols prove to be viable nucleophiles, opening up new opportunities one-pot construction oligosaccharides. power this approach is highlighted by the assembly tri-, hexa-, nonasaccharides composed β-(1 → 6)-glucosaminosyl residues based on preparation triglucosaminosyl thioglycoside DNs, phthaloyl, 2,2,2-trichloroethoxycarbonyl protecting groups amino groups. These glycans potential antigens developing glycoconjugate vaccines against microbial infections.