An Anomeric Base-Tolerant Ester of 8-Alkynyl-1-naphthoate for Gold(I)-Catalyzed Glycosylation Reaction
作者机构：Zhongshan Institute for Drug DiscoveryShanghai Institute of Materia MedicaChinese Academy of SciencesZhongshanGuangdong528400 China Key Laboratory of Medicinal Chemistry for Natural ResourceMinistry of EducationYunnan Provincial Center for Research&Development of Natural ProductsSchool of Chemical Science and TechnologyYunnan UniversityKunmingYunnan650091 China State Key Laboratory of Bioorganic and Natural Products ChemistryCenter for Excellence in Molecular SynthesisShanghai Institute of Organic ChemistryUniversity of Chinese Academy of SciencesChinese Academy of SciencesShanghai200032 China
出 版 物：《Chinese Journal of Chemistry》 (中国化学（英文版）)
年 卷 期：2023年第41卷第11期
页 面：1305-1312页
核心收录：
学科分类：07[理学] 070303[理学-有机化学] 0703[理学-化学]
基 金：the financial support from the National Natural Science Foundation of China(22007080) Zhongshan Science and Technology Bureau(CXTD2022012) Youth Innovation Promotion Association of CAS(2020258) grateful to Hi-Level New R&D Institute(2019B090904008) High-Level Innovative Research Institute(2021B0909050003)from Department of Science Technology of Guangdong Province.Prof.Hongbin Zhang(Yunnan University)is appreciated for the assistance on this project.
主 题：Glycosylation Leaving Group Gold Catalysis Anomeric Ester Base Tolerant Carbohydrates
摘 要：Given the extreme complexity and diversity of carbohydrates,efficient approaches to the homogeneous oligosaccharide remain limited.Chemical synthesis represents one of the most reliable methods to access homogeneous samples,which mainly relies on the key glycosylation reaction.Consistent with enormous efforts to develop leaving groups for establishing robust glycosylation protocols,we herein disclose a structurally novel leaving group of 8-phenylethynyl-1-naphthoate that is able to enable efficient glycosylation reactions under the extremely mild condition of gold(I)-catalysis.Notably,the anomeric naphthoate possesses the unprecedent character of base-stability in sharp contrast to the conventional ester groups at anomeric position of carbohydrates,which endows high compatibility with a variety of chemical transformations.Furthermore,the present glycosylation protocol with 8-phenylethynyl-1-naphthoate as leaving group is able to realize minimally protected glycosylation processes.Mechanistic studies reveal a unique structure of 8-phenylethynyl-1-naphthoate that accounts for the reason for these characteristics.
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