Erosion of Stereochemical Control with Increasing Nucleophilicity: O-Glycosylation at the Diffusion Limit - Beaver, Matthew G; Woerpel, K. A (Journal of organic chemistry, 2010)
Keywords: Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides; Carbohydrates. Nucleosides and nucleotides; Chemical reactivity; Chemistry; Chemistry, Organic; Diffusion; Exact sciences and technology; Glycosides - chemistry; Glycosylation; Glyoxylates - chemistry; Kinetics; Kinetics and mechanisms; Molecular Structure; Organic chemistry; Oxygen - chemistry; Physical Sciences; Preparations and properties; Reactivity and mechanisms; Science & Technology; Stereoisomerism; 4,6-O-BENZYLIDENE-DIRECTED BETA-MANNOPYRANOSYLATION; SOLUTION-PHASE; OLIGOSACCHARIDE SYNTHESIS; DIRECT CONSTRUCTION; 2'-CARBOXYBENZYL GLYCOSIDES; DONORS; CONFORMATIONAL-ANALYSIS; STEREOSELECTIVE-SYNTHESIS; OXOCARBENIUM IONS; AQUEOUS-SOLUTION; Kinetic control; Nucleophilic reaction; Ethanol; Oside; Glycosylation; Stereochemistry; Experimental study; Reaction rate; Chemical substitution; Stereoselectivity; Carbenium compounds; Glycoside; SN1 mechanism; Chemical reactivity; Nucleophilic substitution; Nucleophilicity; Nucleophilic addition; Nucleophile