Copper-Catalyzed Glycosylation Protocol Based on 1,4-Naphthoquinone-Derived Thioglycosides
Mengyu Li1, Xi Xiang1, Zijie Zhou1
1Shanghai Frontiers Science Center of TCM Chemical Biology, Innovation Research Institute of Traditional Chinese Medicine, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China.
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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