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ID 115011
Author
Yoshimura, Yuichi Tohoku Medical and Pharmaceutical University
Wakamatsu, Hideaki Tohoku Medical and Pharmaceutical University
Natori, Yoshihiro Tohoku Medical and Pharmaceutical University
Saito, Yukako Tohoku Medical and Pharmaceutical University
Keywords
glycosylation
hypervalent iodine
Lewis acid
nucleoside
oligosaccharide
Content Type
Journal Article
Description
To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4’-thionucleosides, which could be applied for the synthesis of 4’-selenonucleosides as well. The extension of hypervalent iodine-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2’,3’-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.
Journal Title
Beilstein Journal of Organic Chemistry
ISSN
18605397
Publisher
Beilstein-Institut
Volume
14
Start Page
1595
End Page
1618
Published Date
2018-06-28
Rights
This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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language
eng
TextVersion
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departments
Pharmaceutical Sciences