Publication | Closed Access
Copper(II) Triflate: A Versatile Catalyst for the One‐Pot Preparation of Orthogonally Protected Glycosides
50
Citations
37
References
2011
Year
EngineeringComplex OligosaccharidesGlycobiologyOrganic ChemistryChemistryChemical EngineeringVersatile CatalystOrthogonally Protected GlycosidesOrganometallic CatalysisOne‐pot PreparationGlycosylationDiversity-oriented SynthesisCatalysisGlycoside Building BlocksNatural Product SynthesisCatalytic SynthesisBiomolecular EngineeringNatural SciencesCatalyst PreparationCarbohydrate-protein Interaction
Abstract The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one‐pot preparation of orthogonal protected thio‐ and O ‐glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one‐pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes.
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