Abstract
The total synthesis of 6- O-sulfo-sialylparagloboside is described. A suitably protected β- d-Glc pNAc-(1→3)-β- d-Gal p-(1→4)- d-Glc pOSE derivative was glycosylated with an α- d-Neu p5Ac-(2→3)- d-Gal p derived imidate to give the corresponding protected α- d-Neu p5Ac-(2→3)-β- d-Gal p-(1→4)-β- d-Glc pNAc-(1→3)-β- d-Gal p-(1→4)- d-Glc pOSE pentasaccharide derivative. Proper manipulation of the protecting groups of the pentasaccharide afforded the corresponding glycosyl imidate, which was coupled with (2 S,3 R,4 E)-2-azido-3- O-benzoyl-4-octadecene-1,3-diol. Selective reduction of the azido group, N-acylation with octadecanoic acid, 6-O-sulfation of the Glc pNAc residue, and complete removal of the protecting groups gave the desired 6- O-sulfo-sialylparagloboside.
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