Abstract
The ceric(IV) ammonium nitrate (CAN)-mediated radical addition of dimethyl malonate to glycals 1 affords methyl glycosides 2 and ortho esters 3 as main products; the product distribution strongly depends on the substitution pattern at the 1-position, which can be rationalized in terms of the oxidation potentials of the intermediary anomeric radicals.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Catalysis
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Cerium
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Galactose / analogs & derivatives*
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Galactose / chemistry
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Glycosides / chemical synthesis*
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Indicators and Reagents
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Magnetic Resonance Spectroscopy
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Malonates / chemistry*
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Monosaccharides / chemistry*
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Oxidation-Reduction
Substances
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Glycosides
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Indicators and Reagents
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Malonates
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Monosaccharides
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galactal
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Cerium
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ceric ammonium nitrate
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Galactose