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Challenges in the Conversion of Manual Processes to Machine-Assisted Syntheses: Activation of Thioglycoside Donors with Aryl(trifluoroethyl)iodonium Triflimide
Organic Letters ( IF 5.2 ) Pub Date : 2018-01-16 00:00:00 , DOI: 10.1021/acs.orglett.7b03940
Regis C. Saliba 1 , Zachary J. Wooke 1 , Gabriel A. Nieves 1 , An-Hsiang Adam Chu 2 , Clay S. Bennett 2 , Nicola L. B. Pohl 1, 3
Affiliation  

The steps needed to adapt a stable iodonium promoter for use in automated fluorous-assisted solution-phase oligosaccharide synthesis are described. Direct adaptation of the originally reported batch procedure resulted in the formation of an orthoester or protecting group transfer to the glycosyl acceptor. Fortunately, the addition of inexpensive β-pinene as an acid scavenger avoided both of these side reactions. The utility of this newly developed protocol was applied to the automated solution-phase synthesis of a β-glucan fragment.

中文翻译:

手动工艺向机器辅助合成转化的挑战:芳基(三氟乙基)碘化三氟甲磺酸酯激活硫代糖苷供体

描述了使稳定的碘鎓促进剂适用于自动化的氟辅助溶液相低聚糖合成所需的步骤。最初报道的分批方法的直接适应导致原酸酯或保护基转移至糖基受体的形成。幸运的是,添加廉价的β-pine烯作为除酸剂避免了这两个副反应。此新开发的协议的实用程序应用于β-葡聚糖片段的自动溶液相合成。
更新日期:2018-01-16
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