Synthesis of cyclic α-1,4-oligo--acetylglucosamine 'cyclokasaodorin' a one-pot electrochemical polyglycosylation-isomerization-cyclization process

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 polyglycos...

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Published inChemical communications (Cambridge, England) Vol. 58; no. 57; pp. 7948 - 7951
Main Authors Endo, Hirofumi, Ochi, Masaharu, Rahman, Md Azadur, Hamada, Tomoaki, Kawano, Takahiro, Nokami, Toshiki
Format Journal Article
Published 14.07.2022
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Summary: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'. The first synthesis of the N -acetylglucosamine analogue of α-cyclodextrin has been achieved using the one-pot electrochemical polyglycosylation-isomerization-cyclization process as a key step.
Bibliography:https://doi.org/10.1039/d2cc02287g
Electronic supplementary information (ESI) available: Experimental procedures and spectral data of new compounds. See DOI
ISSN:1359-7345
1364-548X
DOI:10.1039/d2cc02287g