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通过简单的 2-O-苯甲酰基-3,4,6-三-O-苄基保护作用,使常见糖基供体超功能化。

Superarming common glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.

机构信息

Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.

出版信息

J Org Chem. 2010 Feb 19;75(4):1095-100. doi: 10.1021/jo9021474.

Abstract

A complementary concept for superarming glycosyl donors through the use of common protecting groups was previously discovered with S-benzoxazolyl (SBox) glycosyl donors. As this strategy can be of benefit to existing oligosaccharide methodologies, it has now been expanded to encompass a wide array of common, stable glycosyl donors. The versatility of this developed technique has been further illustrated in application to a sequential chemoselective oligosaccharide synthesis, wherein a superarmed ethyl thioglycoside was incorporated into the conventional armed-disarmed strategy.

摘要

先前已经发现,通过使用常见的保护基,可以对 S-苯并恶唑基(SBox)糖基供体进行超活化,这是一个补充概念。由于该策略对现有的寡糖方法学有益,因此现在已将其扩展到涵盖广泛的常见、稳定的糖基供体。该开发技术的多功能性在连续化学选择性寡糖合成中的应用中得到了进一步说明,其中超武装的乙基硫代糖苷被整合到传统的武装-解除武装策略中。

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