Synthesis of Reverse Glycosyl Fluorides and Rare Glycosyl Fluorides Enabled by Radical Decarboxylative Fluorination of Uronic Acids
Synthesis of Reverse Glycosyl Fluorides and Rare Glycosyl Fluorides Enabled by Radical Decarboxylative Fluorination of Uronic Acids
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糖醛酸自由基脱羧氟化合成反糖基氟化物和稀有糖基氟化物
DOI：
10.1021/acs.orglett.0c03514
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发表时间：
2020-12-04
期刊：
影响因子：
5.2
通讯作者：
Li, Ming
中科院分区：
文献类型：
--
作者：
Chen, Pengwei;Wang, Peng;Li, Ming
介绍了一种合成反式糖基氟化物的有效方法，该方法依赖于银促进的结构不同的五氟呋喃和六氢吡喃尿酸在温和的反应条件下的脱羧基氟化反应。通过将易得的D-糖醛酸衍生物通过从C1到C5的切换策略转化为罕见的D-/L-糖基氟化物，进一步展示了该反应的潜在应用。脱羧基氟化引发的烯丙基α-D-C-葡萄糖吡喃尿酸的5-外触发自由基环化反应证实了该反应机理。
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.