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Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosa...

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Detalles Bibliográficos
Autores principales: Rahman, Md Azadur, Kuroda, Kana, Endo, Hirofumi, Sasaki, Norihiko, Hamada, Tomoaki, Sakai, Hiraku, Nokami, Toshiki
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9443410/
https://www.ncbi.nlm.nih.gov/pubmed/36105733
http://dx.doi.org/10.3762/bjoc.18.117
Descripción
Sumario:The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosaccharides up to the octasaccharide by repeating electrolysis with additional monomers. The mechanism of the electrochemical polyglycosylation is also discussed, based on the oxidation potential of the monomer and oligosaccharides.