Open AccessElectrochemical Glycosylation as an Enabling Tool for the Stereoselective Synthesis of Cyclic Oligosaccharides
Author(s) -
Manmode Sujit,
Tanabe Shichidai,
Yamamoto Takashi,
Sasaki Norihiko,
Nokami Toshiki,
Itoh Toshiyuki
Publication year - 2019
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201900185
Subject(s) - glycosylation , chemistry , electrochemistry , intramolecular force , oligosaccharide , combinatorial chemistry , chemical synthesis , stereochemistry , organic chemistry , biochemistry , in vitro , electrode
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.