Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of GlcNAcp- β-(1→3)-Galp- α-(1→2)-6-deoxy-altroHepp- α-(1→O-propyl, an O-Antigenic Repeating Unit from C. jejuni O:23 and O:36

  • Published : 2004.02.20
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Abstract

A trisaccharide, GlcNAcp- ${\beta}-(1{\to}3)-Galp-{\alpha}-(1{\to}2)$-6-deoxy-altroHepp- ${\alpha}-(1{\to}O$-propyl, as an O-antigenic repeating unit of C. jejuni serotype O:23 and O:36 was synthesized. Coupling of the GlcNPhth-(1${\to}$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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