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钴催化的糖烯的高度α-立体选择性糖基化反应

Cobalt-Catalyzed Highly α-Stereoselective Glycosylation of Glycals.

作者信息

Liu Xing-Le, Mu Qiu-Qi, Xu Li, Cai Xin, Li Chang-Jiang, Zheng Zu-Biao, Zhang Hui-Hui, Wang Ai-Dong, Xu Li-Wen

机构信息

School of Chemistry and Chemical Engineering, Northwestern Polytechnical University, Xi'an, Shaanxi 710072, P. R. China.

School of Chemistry and Chemical Engineering, Huangshan University, Huangshan, Anhui 245041, P. R. China.

出版信息

Org Lett. 2024 Dec 6;26(48):10248-10252. doi: 10.1021/acs.orglett.4c03637. Epub 2024 Nov 22.

Abstract

Following the satisfactory catalytic performance of cobalt in the -glycosylation of glycals, further study of cobalt's application values was performed under mild conditions, leading to a range of highly α-stereoselective 2,3-unsaturated , , and glycosides. The synthetic potential of the developed protocol was underscored by the late-stage functionalization of pharmaceutically relevant molecules including the canagliflozin derivative (a potential candidate for treating type 2 diabetes and alleviating pathological aging). Furthermore, control experiments were conducted to elucidate a reasonable mechanism and rule out the pathway involving the configuration conversion between and anomers.

摘要

在钴在糖烯的α-糖基化反应中展现出令人满意的催化性能之后,我们在温和条件下对钴的应用价值进行了进一步研究,从而得到了一系列具有高度α-立体选择性的2,3-不饱和糖苷、吡喃糖苷和呋喃糖苷。所开发方案的合成潜力通过包括卡格列净衍生物(一种治疗2型糖尿病和缓解病理性衰老的潜在候选药物)在内的药学相关分子的后期官能化得以凸显。此外,还进行了对照实验以阐明合理的反应机理,并排除涉及异头物之间构型转化的途径。

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