Microwave-assisted synthesis of N-glycolylneuraminic acid derivatives

作者：Chopra Pradeep; Madge Paul D; Thomson Robin J; Grice I Darren; von Itzstein Mark^*

来源：Tetrahedron Letters, 2013, 54(41): 5558-5561.

DOI：10.1016/j.tetlet.2013.07.107

• Sialic acid
• Microwave
• de-N-acetylation
• N-Glycolylneuraminic
• alpha-2,8-Polysialic acid

A rapid, efficient and scalable synthesis of biologically-relevant N-glycolylneuraminic acid derivatives from the natural N-acetyl (Neu5Ac) precursors has been developed. Microwave irradiation provides accelerated de-N-acetylation compared to more traditional methods, with optimised NaOH-promoted de-N-acetylation in only 15 min. The prepared amines were readily re-N-acylated to afford the corresponding N-glycolyl (Neu5Gc) analogues.

• 出版日期2013-10-9