Electrochemical generation of glycosyl triflate pools.
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.
Nokami
Toshiki
T
Department of Synthetic Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.
Shibuya
Akito
A
Tsuyama
Hiroaki
H
Suga
Seiji
S
Bowers
Albert A
AA
Crich
David
D
Yoshida
Jun-ichi
J
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
D002241:Carbohydrates; D006027:Glycosides; D008698:Mesylates; D013438:Sulfhydryl Compounds; C012077:trifluoromethanesulfonic acid; D008358:Mannose; D005690:Galactose; D000432:Methanol
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