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Review | Regular issue | Vol 94, No. 9, 2017, pp.1625-1651
Published online, 13th July, 2017
DOI: 10.3987/REV-17-865
Development of a Glycosylation Reaction: A Key to Accessing Structurally Unique Nucleosides

Yuichi Yoshimura*

*Faculty of Pharmaceutical Sciences, Tohoku Medical and Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan

Abstract

Nucleosides are potential drug candidates for antitumor and antiviral chemotherapies. Thus, the synthesis of structurally diverse nucleosides would contribute to the search for new antitumor and antiviral agents. The use of the glycosylation reaction to synthesize nucleoside derivatives would be a practical way to prepare nucleosides with unnatural sugar moieties. Therefore, we synthesized many nucleoside derivatives by using new glycosylation reactions categorized into three types: 1) a Pummerer-type glycosylation reaction used for constructing 4’-thionucleoside skeletons, 2) a sulfur-assisted Mitsunobu reaction used for isonucleoside syntheses, and 3) an oxidative coupling reaction catalyzed by hypervalent iodine for carbocyclic nucleosides and in the syntheses of dihydropyranonucleosides. In this review, we describe the development of the glycosylation reactions and their application to the synthesis of various structurally unique nucleoside derivatives.