Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation

The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisacchari...

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Published inBeilstein journal of organic chemistry Vol. 20; no. 1; pp. 1421 - 1427
Main Authors Rahman, Md Azadur, Endo, Hirofumi, Yamamoto, Takashi, Okushiba, Shoma, Sasaki, Norihiko, Nokami, Toshiki
Format Journal Article
LanguageEnglish
Published Germany Beilstein-Institut 26.06.2024
Subjects
Chemistry
cyclic oligosaccharide
electrochemical glycosylation
Full Research Paper
glucosamine
polyglycosylation
electrochemical glycosylation
glucosamine
polyglycosylation
cyclic oligosaccharide
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Abstract The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisaccharide were obtained using the monomer with a 2-azido-2-deoxy group.
AbstractList The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisaccharide were obtained using the monomer with a 2-azido-2-deoxy group.
The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisaccharide were obtained using the monomer with a 2-azido-2-deoxy group.The synthesis of protected precursors of cyclic β-1,6-oligoglucosamines from thioglycosides as monomers is performed by electrochemical polyglycosylation. The monomer with a 2,3-oxazolidinone protecting group afforded the cyclic disaccharide exclusively. Cyclic oligosaccharides up to the trisaccharide were obtained using the monomer with a 2-azido-2-deoxy group.
Author Yamamoto, Takashi
Sasaki, Norihiko
Nokami, Toshiki
Rahman, Md Azadur
Okushiba, Shoma
Endo, Hirofumi
AuthorAffiliation 1 Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
2 Center for Research on Green Sustainable Chemistry, Faculty of Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
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– name: 1 Department of Chemistry and Biotechnology, Tottori University, 4-101 Koyamacho-minami, Tottori city, 680-8552 Tottori, Japan https://ror.org/024yc3q36 https://www.isni.org/isni/0000000106635064
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Keywords electrochemical glycosylation
glucosamine
polyglycosylation
cyclic oligosaccharide
Language English
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Copyright © 2024, Rahman et al.
This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
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cyclic oligosaccharide
electrochemical glycosylation
Full Research Paper
glucosamine
polyglycosylation
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Title Synthesis of cyclic β-1,6-oligosaccharides from glucosamine monomers by electrochemical polyglycosylation
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