糖基二硫代亚氨基碳酸酯在光诱导脱硫交叉偶联反应中的探索
Exploration of Glycosyl Dithioimidocarbonates in Photoinduced Desulfurative Cross-Coupling Reactions.
作者信息
Zhang Ji, Liu Qi, Chiang Angus, Nitz Mark
机构信息
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, ON M5S3H6, Canada.
出版信息
Org Lett. 2024 Oct 11;26(40):8498-8502. doi: 10.1021/acs.orglett.4c03035. Epub 2024 Sep 30.
PMID:39348920
Abstract
Readily synthesized bench-stable glycosyl dithioimidocarbonates are useful -glycoside precursors. Under mild photochemical conditions, these glycosides undergo desulfurative glycosyl radical generation in the presence of weak acid, 4CzIPN, and Hantzsch ester. These radicals perform well in Geise-like reactions to yield -glycosides with high stereoselectivity.
摘要
易于合成且在实验室条件下稳定的糖基二硫代亚氨基碳酸酯是有用的β-糖苷前体。在温和的光化学条件下，这些糖苷在弱酸、4CzIPN和汉斯酯存在下会发生脱硫糖基自由基生成反应。这些自由基在类盖斯反应中表现良好，能以高立体选择性生成β-糖苷。
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