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The first direct method for C-glucopyranosyl derivatization of 2,3,4,6-tetra-O-benzyl-D-glucopyranose
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1987
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Combinatorial ChemistryBioorganic ChemistryBiochemistryNatural SciencesLewis AcidsMedicineGlycobiologyCorresponding β-AnomersBioconjugationOrganic ChemistrySynthetic ChemistryVarious SilylPharmacologyFirst Direct MethodBiomolecular EngineeringGlycosylation
Commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose, activated by trifluoroacetic anhydride reacts, in the presence of Lewis acids, with various silyl enol ethers or with allylsilane to yield C-D-glucopyranosyl derivatives of the α-configuration, and with activated aromatic nucleophiles to yield the corresponding β-anomers.