Synthesis of GlcNAcp-beta-(1 -> 3)-Galp-alpha-(1 -> 2)-6-deoxy-altroHepp-alpha-(1 -> O-propyl, an O-antigenic repeating unit from C-jejuni O : 23 and O : 36

초록

A trisaccharide, GlcNAcp-beta-(1-->3)-Galp-alpha-(1-->2)-6-deoxy-altroHepp-alpha-(1-->O-propyl, as an O-antigenic repeating unit of C. jejuni serotype 0:23 and 0:36 was synthesized. Coupling of the GlcNPhth-(1-->3)-Gal disaccharide donor with allyl 6-deoxy-altroHep acceptor in the presence of iodonium dicollidine Perchlorate (IDCP) promoter afforded the alpha-galactosidic trisaccharide with high stereoselectivities. Subsequent deacetalation, dephthaloylation, N-acetylation, and hydrogenolytic debenzylation furnished the title compound.

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