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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