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.
Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Shinkiti
S
Suzuki
Kouichi
K
Matsumoto
Kohsuke
K
Kawamura
Seiji
S
Suga
Jun-ichi
J
Yoshida
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