Stereoselective Synthesis of a C-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of C-Analogues of Polysialic acids
Stereoselective Synthesis of a C-Linked Neuraminic Acid Disaccharide: Potential Building Block for the Synthesis of C-Analogues of Polysialic acids
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DOI：
10.1021/jo801946y
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发表时间：
2008-12-05
影响因子：
3.6
通讯作者：
Linhardt, Robert J.
中科院分区：
文献类型：
--
作者：
Kim, Jin-Hwan;Huang, Fei;Linhardt, Robert J.
通过钐介导的偶联反应，以非对映选择性的方式从砜供体和醛受体合成C-连接的神经氨酸二糖，所述醛受体被保护为炔丙基醚。所得二糖具有缩醛和苯硫醚官能团C基团，其可以通过光解和氧化反应容易地转化为醛和苯砜基团，以分别充当二糖受体和供体。
C-Linked neuraminic acid disaccharide was synthesized in a diastereoselective manner from a sulfone donor and aldehyde acceptor, which was protected as a propargyl ether, through a samarium-mediated coupling reaction. The resulting disaccharide has acetal and phenyl sulfide functional C groups that can be easily converted into aldehyde and phenyl sulfone groups by photolysis and oxidation reactions to serve as disaccharide acceptor and donor, respectively.