4-氨基-N(5)-乙酰基-4-脱氧神经氨酸的高效合成及其在唾液酸C-4修饰中的应用。
Efficient synthesis of 4-amido-N(5)-acetyl-4-deoxyneuraminic acid and its application to the C-4 modification of sialic acids.
作者信息
Gao Zheng-Xi, Wang Meng, Wang Shaozhong, Yao Zhu-Jun
机构信息
State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.
出版信息
Org Lett. 2009 Aug 20;11(16):3678-81. doi: 10.1021/ol901511x.
A straightforward synthesis of 4-amido-N(5)-acetyl-4-deoxyneuraminic acid, a key precursor to various 4-amidoneuraminic acid analogues, has been achieved using a highly regioselective and diastereoselective [3 + 2]-cycloaddition of d-mannose-derived nitrone with methyl acrylate. Advantages of this newly developed synthesis include the use of economically available materials and reagents, the ease of operations and the excellent control of stereochemistry, as well as the convenience in application to the C-4 modifications of sialic acids.
通过使用源自d-甘露糖的硝酮与丙烯酸甲酯进行高度区域选择性和非对映选择性的[3 + 2]环加成反应，实现了4-氨基-N(5)-乙酰基-4-脱氧神经氨酸（各种4-氨基神经氨酸类似物的关键前体）的直接合成。这种新开发的合成方法的优点包括使用经济易得的材料和试剂、操作简便、立体化学控制出色，以及便于应用于唾液酸的C-4修饰。
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