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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 2
BKCSDE 25(2)
February 20, 2004 

Synthesis of GlcNAcp- β-(1→3)-Galp- α-(1→2)-6-deoxy-altroHepp- α-(1→O-propyl, an O-Antigenic Repeating Unit from C
Shinsook Yoon, Youngsook Shin, Keun Ho Chun, Jeong E. Nam Shin*
Altroheptose, Trisaccharide, Campylobacter jejuni, Antigenic repeating unit
A trisaccharide, GlcNAcp- β-(1→3)-Galp- α-(1→2)-6-deoxy-altroHepp- α-(1→O-propyl, as an O-antigenic repeating unit of C. jejuni serotype O:23 and O: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 α-galactosidic trisaccharide with high stereoselectivities. Subsequent deacetalation, dephthaloylation, N-acetylation, and hydrogenolytic debenzylation furnished the title compound.
289 - 292
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