Angewandte Chemie · 2015 · 19 citations · 26 references
PharmacyBiochemistryMedicinal ChemistryCarbohydrate BiochemistryCarbohydrate ChemistrySynthetic Medicinal ChemistryCarbohydrate SynthesisGlycan StructureGlycosidic Bond FormationGlycosylation PathwaysFlavonoid GlycosylationGlycoside SynthesisGlycosyl Donor ActivationGlycosyl Donor ProtectionGlycosyl Donor ReactivityGlycosyl Donor SynthesisNatural Product Total SynthesisRegioselective Synthesis
Abstract Short total syntheses of natural glycosides (ellagitannins) were performed through sequential and regioselective functionalization of the hydroxy groups of unprotected glucose. The key reactions are β‐selective glycosidation of a gallic acid derivative by using unprotected glucose as a glycosyl donor and catalyst‐controlled regioselective introduction of a galloyl group into the inherently less reactive hydroxy group of the glucoside.
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Regioselective one-pot protection of carbohydrates
Cheng‐Chung Wang, Jinq‐Chyi Lee, Shun‐Yuan Luo et al. · Nature · 2007 · 367 citations
Takuo Okuda, Takashi Yoshida, Mariko Ashida et al. · Journal of the Chemical Society Perkin Transactions 1 · 1983 · 157 citations