Organic Letters · 2015 · 45 citations · 21 references
Bioorganic ChemistryEngineeringGlycobiologyOrganic ChemistryPolysaccharideEnzymatic ModificationBiosynthesisSynthetic ChemistryGlycosylationExcess ReagentBiochemistryBiocatalysisDeacylation ReactionAnomeric Deacylation ReactionsBiomolecular EngineeringNatural SciencesBiotechnologyVersatile ReagentCarbohydrate-protein Interaction
Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.
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