（±）-3-硫代谷氨酸的全合成
Total Synthesis of (±)-3-Thiaglutamate.
作者信息
Chen Hao, Kim Sohjeong, Ting Chi P
机构信息
Department of Chemistry, Brandeis University, 415 South St. Waltham, MA, 02453, United States.
出版信息
Tetrahedron Lett. 2024 Oct 6;149. doi: 10.1016/j.tetlet.2024.155246. Epub 2024 Aug 13.
Abstract
The total synthesis of (±)-3-thiaglutamate is reported. Central to our strategy is an thiol addition to an imine to form the thioaminal of the natural product. The resulting thioaminal product is then subjected to triflic acid global deprotection to produce 3-thiaglutamate as a triflate salt. This work constitutes the first total synthesis of 3-thiaglutamate and demonstrates that the hemithioaminal group in 3-thiaglutamate can be stabilized under acidic conditions.
摘要
报道了（±）-3-硫代谷氨酸的全合成。我们策略的核心是硫醇加成到亚胺上以形成天然产物的硫代氨基。然后将所得的硫代氨基产物进行三氟甲磺酸全局脱保护，以生成三氟甲磺酸盐形式的3-硫代谷氨酸。这项工作构成了3-硫代谷氨酸的首次全合成，并证明了3-硫代谷氨酸中的半硫代氨基基团在酸性条件下可以稳定存在。
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