Angewandte Chemie International Edition in English · 1987 · 61 citations · 8 references
PharmacyBiochemistryChemistryCarbohydrate BiochemistryCarbohydrate ChemistryNatural Product BiosynthesisCarbohydrate DerivatizationCarbohydrate SynthesisGlycan BiosynthesisGlycosidic Bond FormationMonosaccharide ChemistryDeoxy Sugar ChemistryGlycoside SynthesisGlycosyl HalidesSelective MigrationStereochemistry Of Sugar DerivativesStereoselective Sugar Synthesis
2-Deoxy sugars are now directly accessible from 1-glycosyl halides: glycosyl radicals generated with Bu3SnH rearrange in accordance with 1 → 2 into the 2-deoxy sugars. Glycosyl dihalides afford the corresponding dideoxy sugars. C⊙ in 1 and 2 denotes C-1 and C-2, respectively, of a carbohydrate.
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Chryssostomos Chatgilialoglu, K. U. Ingold, J. C. Scaiano · Journal of the American Chemical Society · 1981 · 341 citations