Synthesis of cyclic α-1,4-oligo- N -acetylglucosamine ‘cyclokasaodorin’ via 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
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 14.07.2022
Royal Society of Chemistry
Subjects
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
electrochemistry
electrosynthesis
glycosylation
Isomerization
N-acetylglucosamine
Oligosaccharides
Physical Sciences
Science & Technology
GLYCOSYLATION
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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’.
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ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/D2CC02287G