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
作者： Chen, Pengwei 1 ; Wang, Peng 1 ; Long, Qing 1 ; Ding, Han 1 ; Cheng, Guoqiang 1 ; Li, Tiantian 1 ; Li, Ming 1 ;
作者机构： 1.Ocean Univ China, Sch Med & Pharm, Key Lab Marine Med, Chinese Minist Educ, Qingdao 266003, Peoples R China
2.Chinese Acad Trop Agr Sci, Hainan Key Lab Res & Dev Nat Prod Li Folk Med, Inst Trop Biosci & Biotechnol, Haikou 571101, Hainan, Peoples R China
3.Pilot Natl Lab Marine Sci & Technol, Lab Marine Drugs & Bioprod, Qingdao 266237, Peoples R China
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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