Glycosyl sulfonium ions as storable intermediates for glycosylations
Toshiki Nokami1, Yuki Nozaki, Yoshihiro Saigusa
1Department of Synthetic Chemistry, Biological Chemistry, Graduate School of Engineering, Kyoto University, Nishikyo-ku, Kyoto 615-8510, Japan.
Abstract:
Glycosyl sulfonium ions, which serve as persistent glycosyl cation equivalents, were prepared by the addition of diorganosulfides to an electrochemically generated glycosyl triflate. Low-temperature and variable-temperature NMR studies were performed to reveal the structure, stability, and reactivity of glycosyl sulfonium ions. The glycosyl sulfonium ions could be used as storable intermediates for reactions with various glycosyl acceptors including thioglycosides to give the corresponding disaccharides.
Related Concept Videos
Oligosaccharide Assembly
Multiple sugar molecules that may or may...
Preparation and Reactions of Sulfides
Preparation and Reactions of Thiols
Drug Metabolism: Phase II Reactions
Phase II Reactions: Sulfation and Conjugation with α-Amino Acids
Biosynthesis of Polysaccharides


