Gold(I)-Catalyzed Glycosylation with Glycosyl o-Alkynylbenzoates as Donors

Accounts of Chemical Research
Biao Yu

Abstract

Naturally occurring glycans and glycoconjugates have extremely diverse structures and biological functions. Syntheses of these molecules and their artificial mimics, which have attracted the interest of those developing new therapeutic agents, rely on glycosylation methodologies to construct the various glycosidic linkages. In this regard, a wide array of glycosylation methods have been developed, and they mainly involve the substitution of a leaving group on the anomeric carbon of a glycosyl donor with an acceptor (a nucleophile) under the action of a particular promoter (usually a stoichiometric electrophile). However, glycosylations involving inherently unstable or unreactive donors/acceptors are still problematic. In those systems, reactions involving nucleophilic, electrophilic, or acidic species present on the leaving group and the promoter could become competitive and detrimental to the glycosylation. To address this problem, we applied the recently developed chemistry of alkynophilic gold(I) catalysts to the development of new glycosylation reactions that would avoid the use of the conventional leaving groups and promoters. Gratifyingly, glycosyl o-alkynylbenzoates (namely, glycosyl o-hexynyl- and o-cyclopropylethynylbe...Continue Reading

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Citations

Jul 19, 2018·Chemical Communications : Chem Comm·Xu DongLiming Zhang
Nov 2, 2018·Angewandte Chemie·Fumihiko YoshimuraKeiji Tanino
Jun 21, 2018·Natural Product Reports·Kaiqing MaMingji Dai
Apr 11, 2019·Dalton Transactions : an International Journal of Inorganic Chemistry·Yongjia LinYuanzhi Xia
Jan 23, 2018·Angewandte Chemie·Shengyang WangBiao Yu
Jun 10, 2020·Chemical Communications : Chem Comm·Nasrina ParvinShabana Khan
Sep 20, 2019·Asian Journal of Organic Chemistry·Jesse Ling, Clay S Bennett
Dec 14, 2018·Natural Product Reports·Guozhi XiaoBiao Yu
Sep 11, 2019·Faraday Discussions·Lucie JašíkováJana Roithová
Oct 8, 2019·Chemical Science·Alexander R RoviraRichmond Sarpong
Feb 11, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Kevin Muru, Charles Gauthier
Mar 31, 2021·The Journal of Organic Chemistry·Dennis P A WanderJeroen D C Codée
Apr 10, 2021·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Biao Yu, Shengyang Wang
Mar 17, 2019·Carbohydrate Research·Xin LiuJian-Song Sun
Jul 9, 2021·Dalton Transactions : an International Journal of Inorganic Chemistry·Moushakhi Ghosh, Shabana Khan
Jul 29, 2021·Journal of the American Chemical Society·Xu MaLiming Zhang
Aug 13, 2021·Organic Letters·Yingjie Wang, Biao Yu
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Giulio FittolaniMartina Delbianco
Jun 23, 2018·Journal of the American Chemical Society·K C NicolaouLawrence B Alemany
Apr 24, 2019·Organic Letters·Hiromu HattoriKarl Gademann
Jun 29, 2018·Chemical Reviews·Matteo PanzaAlexei V Demchenko
Oct 20, 2020·Organic Letters·Zhi-Yong ZengJian-Song Sun
Sep 15, 2020·The Journal of Organic Chemistry·Xiaofei ShaoBiao Yu

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