The Chemistry of Isopropenyl Glycopyranosides. Transglycosylations and Other Reactions
The Journal of Organic Chemistry1996Vol. 61(15), pp. 5024–5031
Citations Over TimeTop 16% of 1996 papers
Abstract
Various anomerically pure isopropenyl α- and β-glycopyranosides have been synthesized and shown to undergo synthetically useful transglycosylation reactions with a variety of primary and secondary carbohydrate alcohols. Although stable when stored, isopropenyl glycosides are readily activated as glycosyl donors by a variety of electrophiles, including N-iodosuccinimide/triflic acid, trimethylsilyl triflate, and triflic anhydride. Under conditions that retard formation of the glycosyl cation, the reactivity of isopropenyl glycosides is diverted away from transglycosylation and toward electrophilic addition across the vinyl ether double bond.
Related Papers
- → Trimethylsilyl trifluoromethanesulfonate as an effective catalyst for glycoside synthesis(1981)235 cited
- → An extremely fast and efficient acylation reaction of alcohols with acid anhydrides in the presence of trimethylsilyl trifluoromethanesulfonate as catalyst(1996)89 cited
- → The Use of Bis-trimethylsilyl-acetamide and -urea in Trimethylsilyl Trifluoromethanesulfonate Catalysed Reactions(1993)12 cited
- → Facile Procedure for Acetalization Using Diols, Alkoxysilane and a Catalytic Amount of Trimethylsilyl Trifluoromethanesulfonate(1995)20 cited
- → Lewis Acid Catalyzed Addition of Alkenylzirconocenes to Carbonyl Compounds: Remarkable Activity of Trimethylsilyl Triflate.(2004)