Regiodivergent Functionalization of Protected and Unprotected Carbohydrates using Photoactive 4‐Tetrafluoropyridinylthio Fragment as an Adaptive Activating Group

作者：Shen Cao, Haobo Zhang, Mingshuo Chen, Niming Zhu, Bei‐Bei Zhan, Peng Xu, Xiaoping Chen, Biao Yu, Xiaheng Zhang · 发表于：Angewandte Chemie International Edition · 年份：2024 · DOI：10.1002/anie.202412436 · 被引用次数：29 · 研究领域：Fluorine in Organic Chemistry、Carbohydrate Chemistry and Synthesis

The selective functionalization of carbohydrates holds a central position in synthetic carbohydrate chemistry, driving the ongoing quest for ideal approaches to manipulate these compounds. In this study, we introduce a general strategy that enables the regiodivergent functionalization of saccharides. The use of electron-deficient photoactive 4-tetrafluoropyridinylthio (SPyf) fragment as an adaptable activating group, facilitated efficient functionalization across all saccharide sites. More importantly, this activating group can be directly installed at the C1, C5 and C6 positions of biomass-derived carbohydrates in a single step and in a site-selective manner, allowing for the efficient and precision-oriented modification of unprotected saccharides and glycans.