使用糖基 N-(邻甲氧基苯基)三氟乙酰亚胺酯的 α-选择性糖基化反应。
α-Selective glycosylations using glycosyl N-(ortho-methoxyphenyl)trifluoroacetimidates.
机构信息
Department of Chemistry, University of Copenhagen, Universitetsparken 5, DK-2100 Copenhagen, Denmark.
出版信息
Org Biomol Chem. 2020 Mar 11;18(10):1918-1925. doi: 10.1039/c9ob02696g.
Six N-(o-methoxyphenyl)trifluoroacetimidate glycosyl donors have been synthesized and their role as glycosyl donors has been investigated. The donors were synthesized with complete β-selectivity, except in one case, and were found to be stable. When Bi(OTf)3, Fe(OTf)2, and Zn(OTf)2 were employed as catalysts, the glycosylations were found to be highly α-selective in Et2O. The selectivity and reaction rate changed with a change in the acceptor reactivity.
已经合成了六个 N-(邻甲氧基苯基)三氟乙酰亚胺基糖苷供体，并研究了它们作为糖苷供体的作用。除了一个例外，这些供体都是以完全的β选择性合成的，并且被发现是稳定的。当使用 Bi(OTf)3、Fe(OTf)2 和 Zn(OTf)2 作为催化剂时，在 Et2O 中，糖苷化反应被发现是高度α选择性的。选择性和反应速率随受体反应性的变化而变化。
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