Novel glycosylation reactions using glycosyl thioimidates of N-acetylneuraminic acid as sialyl donors

Bioorganic & Medicinal Chemistry Letters
Kiyoshi IkedaMasayuki Sato

Abstract

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.

References

Sep 1, 1995·The Journal of Membrane Biology·C Townsend, R L Rosenberg

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Citations

Apr 13, 2010·Annual Review of Biochemistry·Laura L Kiessling, Rebecca A Splain
Jan 29, 2009·Angewandte Chemie·Xiangming Zhu, Richard R Schmidt

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