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Application of Ortho Esterification under Kinetically Controlled Conditions to the Selective Acylation in the D-Gluco-, D-Ribo- and D-Xylo-furanose Series
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1995
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Selective AcylationBioorganic ChemistryEngineeringGlycobiologyOrganic ChemistryPolysaccharideMild Acid ConditionsChemistryEnzymatic ModificationD-xylo-furanose SeriesGlycosylationBiochemistryBiocatalysisCatalysisAsymmetric CatalysisCatalytic SynthesisBiomolecular EngineeringBiomanufacturingNatural SciencesEnzyme CatalysisVarious GlucofuranosesOrtho Esterification
The ortho esterification of various glucofuranoses in the D-ribo-, D-xylo and D-gluco series under kinetic control was obtained through the action of 1,1-dimethoxyethene (a ketene acetal) on the monosaccharide using mild acid conditions. The selective hydrolysis of the methoxyethylidene derivatives thus obtained, gave access to α-hydroxy acetates which are useful synthetic intermediates.