title: Electrochemical generation of glycosyl triflate pools.
abstract: Glycosyl triflates, which serve as important intermediates in glycosylation reactions, were generated and accumulated by the low-temperature electrochemical oxidation of thioglycosides such as thioglucosides, thiogalactosides, and thiomannosides in the presence of tetrabutylammonium triflate (Bu(4)NOTf) as a supporting electrolyte. Thus-obtained solutions of glycosyl triflates (glycosyl triflate pools) were characterized by low-temperature NMR measurements. The thermal stability of glycosyl triflates and their reactions with glycosyl acceptors were also examined.
authors: Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
authors: Toshiki
authors: T
authors: Nokami
authors: Akito
authors: A
authors: Shibuya
authors: Hiroaki
authors: H
authors: Tsuyama
authors: Seiji
authors: S
authors: Suga
authors: Albert A
authors: AA
authors: Bowers
authors: David
authors: D
authors: Crich
authors: Jun-ichi
authors: J
authors: Yoshida
mesh_terms: D002241:Carbohydrates / Q000737:chemistry; D004563:Electrochemistry; D005690:Galactose / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D008358:Mannose / Q000737:chemistry; D008698:Mesylates / Q000737:chemistry*; D000432:Methanol / Q000737:chemistry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D006027:Glycosides; D008698:Mesylates; D013438:Sulfhydryl Compounds; C012077:trifluoromethanesulfonic acid; D008358:Mannose; D005690:Galactose; D000432:Methanol
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