TY - JOUR A1 - Yoshimura, Yuichi A1 - Wakamatsu, Hideaki A1 - Natori, Yoshihiro A1 - Saito, Yukako A1 - Minakawa, Noriaki T1 - Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 1595 EP - 1618 SN - 1860-5397 DO - 10.3762/bjoc.14.137 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.137 KW - glycosylation KW - hypervalent iodine KW - Lewis acid KW - nucleoside KW - oligosaccharide N2 - 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. ER -