Cyclopropenium Cation Promoted Dehydrative Glycosylations Using 2-Deoxy- and 2,6-Dideoxy-Sugar Donors

Cyclopropenium Cation Promoted Dehydrative Glycosylations Using 2-Deoxy- and 2,6-Dideoxy-Sugar Donors

Dehydrative glycosylation reactions using 2-deoxy- and 2,6-dideoxy-sugar donors promoted by a combination of 3,3-dichloro-1,2-diphenylcyclopropene and tetrabutylammonium iodide (TBAI) are described. The reactions are α-selective and proceed under mild conditions at room temperature without the need...

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Veröffentlicht in:Organic letters 2011-06, Vol.13 (11), p.2814-2817
Hauptverfasser: Nogueira, Jason M, Nguyen, Son Hong, Bennett, Clay S
Format: Artikel
Sprache:eng
Schlagworte:
Carbohydrates - chemistry
Catalysis
Combinatorial Chemistry Techniques
Cyclopropanes - chemistry
Glycosylation
Molecular Structure
Quaternary Ammonium Compounds - chemistry
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Zusammenfassung:Dehydrative glycosylation reactions using 2-deoxy- and 2,6-dideoxy-sugar donors promoted by a combination of 3,3-dichloro-1,2-diphenylcyclopropene and tetrabutylammonium iodide (TBAI) are described. The reactions are α-selective and proceed under mild conditions at room temperature without the need for special dehydrating agents. The reaction is shown to be effective with a number of glycosyl acceptors, including those possessing acid and base sensitive functionality.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol200726v