Glycosylation Using Hemiacetal Sugar Derivatives

O-α-D-Rhamnopyranosyl-(1->3)-O-α-D-rhamnopyranosyl-(1->2)-D-rhamnopyranose, a repeating trisaccharide of the O-specific polysaccharides (OPSs) of Pseudomonades, and O-α-D-tyvelopyranosyl-(1->3)-O-α-D-mannopyranosyl-(1->4)-L-rhamnopyranose, a trisaccharide composing the OPSs of Salmonella...

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Published in:Bulletin of the Chemical Society of Japan 2003-07, Vol.76 (7), p.1409
Main Authors: Hirooka, Motoko, Yoshimura, Asako, Saito, Izumi, Ikawa, Fumio, Uemoto, Yoko, Koto, Shinkiti, Takabatake, Ayano, Taniguchi, Aya, Shinoda, Yoshika, Morinaga, Aya
Format: Article
Language:English
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Summary:O-α-D-Rhamnopyranosyl-(1->3)-O-α-D-rhamnopyranosyl-(1->2)-D-rhamnopyranose, a repeating trisaccharide of the O-specific polysaccharides (OPSs) of Pseudomonades, and O-α-D-tyvelopyranosyl-(1->3)-O-α-D-mannopyranosyl-(1->4)-L-rhamnopyranose, a trisaccharide composing the OPSs of Salmonella typhi, were synthesized by in-situ activating glycosylation reactions using hemiacetal sugar derivatives. Allyl 2,4-di-O-benzyl-α-D-rhamnopyranoside was prepared via the direct ditritylation of allyl α-D-mannopyranoside. 3-O-Acetyl-2,4-di-O-benzyl-D-rhamnopyranose was used as a precursor for the moiety of D-tyvelose (3,6-dideoxy-D-arabino-hexose, 3,6-dideoxy-D-mannopyranose, 3-deoxy-D-rhamnose) of the salmonella trisaccharide.
ISSN:0009-2673
1348-0634