Copper(II) Triflate: A Versatile Catalyst for the One-Pot Preparation of Orthogonally Protected Glycosides
Copper(II) Triflate: A Versatile Catalyst for the One-Pot Preparation of Orthogonally Protected Glycosides
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DOI：
10.1002/adsc.201100228
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发表时间：
2011-10-01
影响因子：
5.4
通讯作者：
Galan, M. Carmen
中科院分区：
文献类型：
--
作者：
Anh-Tuan Tran;Jones, Rachel A.;Galan, M. Carmen
开发制备正交保护的糖苷结构单元的通用和方便的方法对于复杂寡糖的有效合成是必不可少的。在此，我们描述了一种新的方法，使用铜（II）三氟甲磺酸盐作为一个通用的催化剂，从相应的未保护的对应物的正交保护的硫代和O-糖苷的一锅制备。该反应条件温和，易于操作，适用于两步和三步一锅法串联反应，包括亚芳基缩醛化、酯化、区域选择性还原缩醛开环、糖基化和硅烷化反应。
The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one-pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes.