An efficient synthesis of C3 C-alkylated Neu5Ac2en derivatives

作者：Rudrawar Santosh; Pascolutti Mauro; Bhatt Beenu; Thomson Robin J; von Itzstein Mark^*

来源：Tetrahedron Letters, 2013, 54(10): 1198-1201.

DOI：10.1016/j.tetlet.2012.12.064

• Influenza
• Sialidase
• Carbohydrate
• Neu5Ac2en
• Sialic acid

C3-modified Neu5Ac2en derivatives can be used to study the flexible 150-loop region of influenza virus sialidases and also provide a new template for the development of next-generation sialidase inhibitors. This Letter describes an efficient synthetic route towards the large scale synthesis of C3 C-alkylated Neu5Ac2en derivatives. The key intermediate, a 3-eq-allyl-Neu5Ac derivative, is formed by stereoselective addition of the allyl group in an equatorial configuration at C3, regardless of the stereochemistry of the bromohydrin precursor.

• 出版日期2013-3-6