Electrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides

• Published in: ChemistryOpen (Weinheim) Vol. 8; no. 7; pp. 869 - 872
• Main Authors: Manmode, Sujit, Tanabe, Shichidai, Yamamoto, Takashi, Sasaki, Norihiko, Nokami, Toshiki, Itoh, Toshiyuki
• Format: Journal Article
• Language: English
• Published: Germany John Wiley & Sons, Inc 01-07-2019; John Wiley and Sons Inc; Wiley-VCH
• Subjects: automated synthesis; Automation; Carbohydrates; Communication; Communications; cyclic oligosaccharides; electrochemical glycosylation; Electrolytes; glucosamine; Hydroxyl groups; Investigations; Oligosaccharides; Organic chemistry; Stereoselectivity; electrochemical glycosylation; glucosamine; automated synthesis; stereoselectivity; cyclic oligosaccharides
• ISSN: 2191-1363; 2191-1363
• DOI: 10.1002/open.201900185

Electrochemical glycosylation of a linear oligosaccharide with a protecting‐group‐free primary hydroxyl group afforded cyclic oligo‐saccharides, up to hexasaccharides, in high yields. Precursors of the cyclic oligosaccharides were prepared by automated electro‐chemical assembly‐a method for the automated electrochemical solution‐phase synthesis of oligosaccharides. We demonstrated that electrochemical glycosylation is useful not only for intermolecular glycosylation but also for intramolecular glycosylation to synthesize cyclic oligosaccharides.
Electric sugars! Electrochemical glycosylation is useful to synthesize cyclic oligoglucosamines stereoselectively. Precursors of the cyclic oligosaccharides were prepared by automated electrochemical assembly a method for the automated electrochemical solution‐phase synthesis of oligosaccharides.