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Highly Stereoselective Synthesis of Pseudoglycals via Yb(OTf)<sub>3</sub> Catalyzed Ferrier Glycosylation
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2001
Year
Bioorganic ChemistryEngineeringGlycobiologyAnomeric SelectivityBiosynthesisSynthetic ChemistryStereoselective SynthesisGlycosylationBiochemistryBiocatalysisCatalysisNatural Product SynthesisAsymmetric CatalysisEnantioselective SynthesisBiomolecular EngineeringVarious AlcoholsNatural SciencesFerrier RearrangementCarbohydrate-protein Interaction
The reaction of tri-O-acetyl-d-glucal with various alcohols and thiols was effectively promoted by a catalytic amount of Yb(OTf)3 to produce a variety of pseudoglycals via Ferrier rearrangement in excellent yields and anomeric selectivity.