Generation of alkoxycarbenium ion pools from thioacetals and applications to glycosylation chemistry.
[reaction: see text] Alkoxycarbenium ions have been generated and accumulated as "cation pools" by the low-temperature electrochemical oxidation of alpha-phenylthioethers. Although an unsuccessful attempt to accumulate glycosyl cations was made, a one-pot method for electrochemical glycosylation, which involves anodic oxidation of thioglycosides to generate glycosyl cation equivalents followed by their reactions with glycosyl acceptors, has been developed.
Suzuki
Shinkiti
S
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Matsumoto
Kouichi
K
Kawamura
Kohsuke
K
Suga
Seiji
S
Yoshida
Jun-ichi
J
D000080:Acetals / Q000737:chemistry*; D006031:Glycosylation; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry
D000080:Acetals; D006838:Hydrocarbons; C030011:carbene; D008697:Methane