Abstract
The first synthesis of maradolipid, a unique dissymmetrically 6,6'-di-O-acylated trehalose glycolipid isolated from C. elegans, is accomplished in five steps starting from trehalose in 45% overall yield. The short synthesis relies on dissymmetrization of trehalose core via regioselective acylation of a 2,3,4,2',3',4'-hexa-O-TMS trehalose 6,6'-diol derivative as a key step.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acylation
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Animals
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Caenorhabditis elegans / chemistry
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Glycolipids / chemical synthesis*
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Glycolipids / chemistry
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Glycolipids / isolation & purification
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Molecular Sequence Data
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Molecular Structure
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Trehalose / analogs & derivatives
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Trehalose / chemical synthesis*
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Trehalose / chemistry
Substances
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Glycolipids
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maradolipid
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Trehalose