Cyclopropenium Cation Promoted Dehydrative Glycosylations Using 2-Deoxy- and 2,6-Dideoxy-Sugar Donors
2011; American Chemical Society; Volume: 13; Issue: 11 Linguagem: Inglês
10.1021/ol200726v
ISSN1523-7060
AutoresJason M. Nogueira, Son Hong Nguyen, Clay S. Bennett,
Tópico(s)Chemical Synthesis and Analysis
ResumoDehydrative 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.
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