A Strategy for O-Alkylation of Serine and Threonine from Serinyl and Threoninyl Acetic Acids by Photoinduced Decarboxylative Radical Reactions: Connection between Serine/Threonine and Carbohydrates/Amino Acids at the Side Chain
A Strategy for O-Alkylation of Serine and Threonine from Serinyl and Threoninyl Acetic Acids by Photoinduced Decarboxylative Radical Reactions: Connection between Serine/Threonine and Carbohydrates/Amino Acids at the Side Chain
复制标题
通过光诱导脱羧自由基反应从丝氨酰和苏氨酰乙酸中进行丝氨酸和苏氨酸 O-烷基化的策略：丝氨酸/苏氨酸与侧链碳水化合物/氨基酸之间的连接
DOI：
10.1021/acs.joc.8b00061
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发表时间：
2018
期刊：
影响因子：
3.6
通讯作者：
Y. Yoshimi*
中科院分区：
文献类型：
--
作者：
T. Yamamoto;T. Iwasaki;T. Morita;Y. Yoshimi*
丝氨酸和苏氨酸衍生物在羟基上的O-烷基化反应是利用丝氨酸和苏氨酸乙酸与有机光催化剂的光诱导脱羧自由基反应实现的，在温和的条件下没有外消旋化。光诱导脱羧自由基添加的丝氨酸和苏氨酸乙酸的缺电子烯烃提供连接的丝氨酸和苏氨酸与碳水化合物和氨基酸的侧链。此外，在类似的光化学条件下进行了含氘的O-甲基化和丝氨酸的O-苄基化。
O-Alkylations of serine and threonine derivatives at the hydroxy group were achieved using photoinduced decarboxylative radical reactions of serinyl and threoninyl acetic acids with an organic photocatalyst without racemization under mild conditions. Photoinduced decarboxylative radical additions of serinyl and threoninyl acetic acids to electron-deficient alkenes provided linked serine and threonine with carbohydrates and amino acids at the side chain. In addition,O-methylations containing deuterium andO-benzylation of serine were performed under similar photochemical conditions.