Abstract
The de novo synthesis of racemic 1',4'-dimethyluridine was accomplished in 12 steps starting from 2,5-dimethylfuran and vinylene carbonate. Key steps of the sequence include the stereoconvergent preparation of a meso diacid, and a stereoselective glycosylation without neighboring group participation. Such 1',4'-disubstituted ribonucleoside analogues are undisclosed compounds, which may present interesting biological activities.
MeSH terms
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Alcohols / chemistry
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Carbohydrates / chemical synthesis
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Glycosylation
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Heptanes / chemistry
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Heterocyclic Compounds / chemistry
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Hydroxylation
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Models, Molecular
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Molecular Conformation
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Oxidation-Reduction
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Stereoisomerism
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Substrate Specificity
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Uridine / analogs & derivatives*
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Uridine / chemical synthesis*
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Uridine / chemistry*
Substances
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1',4'-dimethyluridine
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Alcohols
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Carbohydrates
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Heptanes
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Heterocyclic Compounds
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Uridine