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A General Procedure for Conversion of S-Glycosyl Isothiourea Derivatives into Thioglycosides, Thiooligosaccharides and Glycosyl Thioesters
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2001
Year
Bioorganic ChemistryGeneral ProcedureBiochemistryGlycosylationNatural SciencesGlycobiologyNatural Product BiosynthesisS-glycosyl Isothiourea DerivativesGlycosyl ThioestersSimple ProcedureChemical DerivativeSynthetic ChemistryEnantioselective SynthesisBiomolecular EngineeringNatural Product Synthesis
A simple procedure for conversion of S-glycosyl isothiourea derivatives into thioglycosides by promotion with triethylamine is described. The reaction conditions allow the synthesis of glycosyl thioesters and some thioglycosides, which cannot be prepared using the traditional approach. The procedure has been successfully applied for preparation of thiooligosaccharides, shown by syntheses of methyl 4-thio-α-cellobioside and methyl 4-thio-α-lactoside derivatives.