Publication | Closed Access
Halide Effects on Cyclopropenium Cation Promoted Glycosylation with Deoxy Sugars: Highly α‐Selective Glycosylations Using a 3,3‐Dibromo‐1,2‐diphenylcyclopropene Promoter
45
Citations
90
References
2012
Year
Bioorganic ChemistryEngineeringGlycobiologyDeoxy SugarsOrganic ChemistryPolysaccharideChemistryReactive Glycosyl DonorsStereoselective SynthesisGlycosylationHalide Effectsα‐Selective Glycosylation ReactionsBiochemistryDiversity-oriented SynthesisAsymmetric CatalysisBio-orthogonal ChemistryBiomolecular EngineeringDonor SugarNatural SciencesHighly α‐Selective GlycosylationsCarbohydrate-protein Interaction
Abstract A mixture of 3,3‐dibromocyclopropene and TBAI promotes highly α‐selective glycosylation reactions (up to >20:1) by using deoxy sugar hemiacetal donors. The reaction provides a convenient method for generating highly reactive glycosyl donors in situ from shelf‐stable starting materials. Both armed and disarmed sugars undergo the reaction, and selectivity is independent of the configuration of the donor sugar.
| Year | Citations | |
|---|---|---|
Page 1
Page 1