Enhanced Sialylating Activity of O-Chloroacetylated 2-Thioethyl Sialosides
- 29 April 2005
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 2005 (9) , 1375-1380
- https://doi.org/10.1055/s-2005-868514
Abstract
It has been shown that O-chloroacetyl protecting groups enhance significantly sialylating activity of 2-thioethyl sialosides in model reactions of α(2-8)-sialylation. Ethyl 4,7,8,9-tetra-O-chloroacetyl-3,5-dideoxy-2-thio-5-trifluoroacetamido-d-glycero-α-d-galacto-non-2-ulopyranoside that combines electron-withdrawing O-chloroacetyl and N-trifluoroacetyl protecting groups displayed the best reactivity and enabled the most efficient synthesis of the Neu5Acα(2-8)Neu5Ac dimer. The GD3 tetrasaccharide was synthesized in stepwise manner using this sialyl donor in the key (2-8)-coupling, albeit the yield was noticeably lower than in the model sialylation of monosaccharide acceptors.Keywords
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