Ikeda Kiyoshi, Aizawa Misato, Sato Kazuki, Sato Masayuki
School of Pharmaceutical Sciences, University of Shizuoka, Surugaku-Yada 52-1, Shizuoka 422-8526, Japan.
Bioorg Med Chem Lett. 2006 May 15;16(10):2618-20. doi: 10.1016/j.bmcl.2006.02.037. Epub 2006 Mar 3.
Novel sialyl donors 4 bearing a thioimidolyl moiety as the leaving group were successfully prepared from the corresponding arylthio derivatives 3 and a peracetylated chloro derivative of Neu5Ac 2 in the presence of N,N-di-isopropylethylamine with moderate yields. The reaction of 4 with various alcohols 5 was effectively activated by AgOTf as the promoter to give the corresponding O-sialosides 6 with good yields. Selective activation of 4a over 4-pentenyl 2-glycoside of Neu5Ac 7 with AgOTf was also achieved.
新型唾液酸供体4带有硫代咪唑基部分作为离去基团，在N,N -二异丙基乙胺存在下，由相应的芳硫基衍生物3和Neu5Ac 2的全乙酰化氯代衍生物成功制备，产率适中。4与各种醇5的反应通过AgOTf作为促进剂有效活化，以良好的产率得到相应的O -唾液酸苷6。还实现了用AgOTf对Neu5Ac 7的4a比4 -戊烯基2 -糖苷的选择性活化。
