Synthesis of Reverse Glycosyl Fluorides and Rare Glycosyl Fluorides Enabled by Radical Decarboxylative Fluorination of Uronic Acids

文献类型： 外文期刊

第一作者： Chen, Pengwei

作者： Chen, Pengwei;Wang, Peng;Long, Qing;Ding, Han;Cheng, Guoqiang;Li, Tiantian;Li, Ming;Chen, Pengwei;Li, Ming

作者机构：

期刊名称：ORGANIC LETTERS （ 影响因子：6.005； 五年影响因子：5.551 ）

ISSN： 1523-7060

年卷期： 2020 年 22 卷 23 期

页码：

收录情况： SCI

摘要： An efficient protocol for synthesizing reverse glycosyl fluorides is described, relying on silver-promoted decarboxylative fluorination of structurally diverse pentofuran- and hexopyranuronic acids under the mild reaction conditions. The potential applications of the reaction are further demonstrated by converting readily available D-uronic acid derivatives into uncommon D-/L-glycosyl fluorides through a C1-to-C5 switch strategy. The reaction mechanism is corroborated by 5-exo-trig radical cyclization of allyl alpha-D-C-glucopyranuronic acid triggered by decarboxylative fluorination.

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