文献类型：期刊文献

英文题名：Insight into gold-catalyzed glycosylation of glycosyl ynenoates

作者：Zhang, Lvfeng[1];Liang, Youling[1];Li, Xiaona[1];Liu, Rongkun[1];Zheng, Jibin[1];Xu, Peng[2];Yu, Biao[2];Yang, You[1,3]

机构：[1]East China Univ Sci & Technol, Engn Res Ctr Pharmaceut Proc Chem, Sch Pharm, Shanghai Key Lab New Drug Design,Shanghai Frontier, Shanghai, Peoples R China;[2]Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Chem Biol, Shanghai, Peoples R China;[3]East China Univ Sci & Technol, Sch Pharm, Room 1035A,Res Bldg 18,130 Meilong Rd, Shanghai 200237, Peoples R China

年份：2024

卷号：43

期号：1-2

起止页码：21

外文期刊名：JOURNAL OF CARBOHYDRATE CHEMISTRY

收录：;EI(收录号：20243917103865);WOS:【SCI-EXPANDED(收录号:WOS:001252417800001)】；

基金：No Statement Available

语种：英文

外文关键词：Alkyne donors; carbohydrates; glycosylation; glycosides; gold

摘要：Gold-catalyzed glycosylation using alkyne donors is a versatile approach for the efficient assembly of diverse types of glycosides due to its catalytic and mild glycosylation properties. Minor structural alterations might significantly affect the glycosylation reaction when the alkyne-based leaving groups are simplified. By mapping the glycosylation reactivities of a series of structurally simplified alkyne donors, herein we demonstrate the role of each characteristic functional group of glycosyl ynenoates. Based on the isolation and the X-ray diffraction characterization of the pyran-5-ylgold(I) complex generated from the leaving group, a plausible mechanism of the gold(I)-catalyzed glycosylation with glycosyl ynenoates as donors was proposed.