8-(Methyltosylaminoethynyl)-1-naphthyl (MTAEN) Glycosides: Potent Donors in Glycosides Synthesis
Si-Yu Zhou, Xin-Ping Hu, Huijuan Liu, Qingju Zhang, Jin‐Xi Liao, Yuan‐Hong Tu, Jiansong Sun
Abstract
With 8-(methyltosylaminoethynyl)-1-naphthyl (MTAEN) glycoside as donors, a novel and efficient glycosylation protocol has been established. The MTAEN glycosylation protocol exhibits the merits of shelf-stable donors, mild catalytic promotion conditions, considerably extended substrate scope encompassing both free alcohols, silylated alcohols, nucleobases, primary amides, and C-type nucleophile acceptors, and applicability to various one-pot strategies for highly efficient synthesis of oligosaccharides, such as orthogonal one-pot, single-catalyst one-pot, and acceptor reactivity-controlled one-pot strategies.
Topics & Concepts
ChemistryGlycosylationNucleophileGlycosideCatalysisCombinatorial chemistrySubstrate (aquarium)Glycosyl donorOne-pot synthesisAcceptorOrganic chemistryStereochemistryBiochemistryGeologyPhysicsCondensed matter physicsOceanographyCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchChemical Synthesis and Analysis