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Highly Stereoselective Synthesis of 2,3-Unsaturated Thioglycopyranosides Employing Molecular Iodine
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2010
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EngineeringBiochemistryNatural SciencesGlycobiologyMolecular IodineOrganic ChemistryVarious ThiolsCarbohydrate-protein InteractionStereoselective SynthesisChemistryNatural Product SynthesisAvailable IodineSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringGlycosylation
Molecular iodine has been utilized for the first time for the thioglycosidation of d-glycals with various thiols to afford the corresponding 2,3-unsaturated thioglycosides in high yields. In the case of tri-O-acetyl-d-glucal, the α-anomer was obtained exclusively. The use of readily available iodine makes this method quite simple, more convenient, and practical.