Abstract
[structures: see text] A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Ascorbic Acid / chemistry*
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Butanols / chemical synthesis*
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Butanols / chemistry
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Catalysis
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Ceramides / chemical synthesis*
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Ceramides / chemistry
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Food Preservatives / chemistry*
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Indicators and Reagents
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Molecular Structure
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Stereoisomerism
Substances
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(S)-3-(hydroxymethyl)butane-1,2,4-triol
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Butanols
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Ceramides
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Food Preservatives
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Indicators and Reagents
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isoascorbic acid
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Ascorbic Acid