Tf2O/TfOH catalytic glycosylation using o-(p-methoxyphenylethynyl)benzyl glycosides as donors and its application in synthesis of oligosaccharides

• Published in: Tetrahedron letters Vol. 116; pp. 154342 - 154346
• Main Authors: Lan, Xinguang, Cai, Chenglin, Wang, Jincai, Zhang, Qi, Feng, Yingle, Chai, Yonghai
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 17.02.2023; Elsevier
• Subjects: Catalytic glycosylation; Chemistry; Chemistry, Organic; Latent-active strategies; Nonmetal catalysis; O-ether glycosides; Oligomannoses; Physical Sciences; Science & Technology; Oligomannoses; O-ether glycosides; Catalytic glycosylation; Nonmetal catalysis; Latent-active strategies; VERSATILE; O -ether glycosides
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2023.154342

A catalytic glycosylation protocol was established using Tf2O or TfOH as catalyst and o-(p-methoxyphenylethynyl)benzyl (MPEB) glycosides as donors. This glycosylation protocol was further applied to the synthesis of a linear hexamannose via ‘latent-active’ strategies. [Display omitted] A catalytic glycosylation protocol was established using Tf2O or TfOH as catalyst and o-(p-methoxyphenylethynyl)benzyl (MPEB) glycosides as donors. The MPEB donors are stable and readily prepared from inexpensive starting material. The donors were activated by 10 mol% Tf2O or TfOH and coupled with various acceptors to provide desired glycosides in modest to good yield. This glycosylation protocol was further applied to the synthesis of linear hexamannose via ‘latent-active’ strategies.