Copper-Catalyzed Glycosylation Protocol Based on 1,4-Naphthoquinone-Derived Thioglycosides

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-02-25 DOI:10.1021/acs.orglett.5c00473

Mengyu Li, Xi Xiang, Zijie Zhou, Xin Zhou, Meifang Yang, Yitian Zhao, Xiangwei Zheng, Houchao Tao

引用次数: 0

Abstract

We report a copper-catalyzed glycosylation protocol utilizing 2-(para-methoxyphenylethynyl)-1,4-naphthoquinone-3-thioglycosides (NQTs) as effective glycosyl donors. These novel donors, characterized by a naphthoquinone scaffold, enable rapid and efficient preparation through a one-pot, two-step synthesis. Additionally, they are efficiently activated by cost-effective Cu(II) salts, facilitating glycosylation with a broad range of substrates. The practicality of NQT donors is further demonstrated by their compatibility with latent-active glycosylation strategies and their applicability in the versatile one-pot synthesis of saccharides.

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.