title: Synthetic carbohydrate research based on organic electrochemistry.
abstract: Development of a novel method for generating glycosyl cations or their equivalents is highly desired, because such intermediates are crucial for developing stereoselective glycosylations in oligosaccharide syntheses. In this review we focus on electrochemical methods that we have recently developed. The anodic oxidation of thioglycosides is effective for generating glycosyl triflate pools, which react with glycosyl acceptors. The reaction of glycosyl triflate pools with diorganosulfides gives glycosyl sulfonium ions, which also serve as effective glycosylation intermediates. The indirect electrochemical method is effective for the generation of glycosyl cations or their equivalents and the use of a flow-microreactor system enables glycosylation using such intermediates.
authors.affiliation: Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Kyotodaigakukatsura, Nishikyo-ku, 615-8510 Kyoto, Japan. tnokami@sbchem.kyoto-u.ac.jp
authors.forename: Toshiki
authors.initials: T
authors.lastname: Nokami
authors.forename: Kodai
authors.initials: K
authors.lastname: Saito
authors.forename: Jun-Ichi
authors.initials: J
authors.lastname: Yoshida
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic / Q000295:instrumentation / Q000379:methods*; D004563:Electrochemistry / Q000295:instrumentation / Q000379:methods*; D004573:Electrolytes / Q000737:chemistry; D006031:Glycosylation; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D002241:Carbohydrates; D004573:Electrolytes; D009844:Oligosaccharides