Synthesis of cyclic α-1,4-oligo-N-acetylglucosamine ‘cyclokasaodorin’ via a one-pot electrochemical polyglycosylation-isomerization-cyclization process

Abstract

Electrochemical synthesis of unnatural cyclic oligosaccharides composed of N-acetylglucosamine with α-1,4-glycosidic linkages has been accomplished. A thioglycoside monomer equipped with the 2,3-oxazolidinone protecting group was used to prepare linear oligosaccharides by electrochemical polyglycosylation. In the same pot, isomerization of the linear oligosaccharides and intramolecular electrochemical glycosylation for cyclization were also conducted sequentially to obtain the precursor of the cyclic α-1,4-oligo-N-acetylglucosamine ‘cyclokasaodorin’.