Synthesis of a xylosylated rhamnose pentasaccharide--the repeating unit of the O-specific side chain of lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18
2002
Zhang, J. | Kong, F.
A xylosylated rhamnose pentasaccharide, alpha-L-Rhap-(1-3)-[beta-L-Xylp-(1-2)-] [beta-L-Xylp-(1-4)-]alpha-L-Rhap-(1-3)-L-Rhap, the repeating unit of the O-specific side chain of the lipopolysaccharides from the reference strains for Stenotrophomonas maltophilia serogroup O18, was synthesized by a highly regio- and stereoselective procedure. Thus coupling of methyl rhamnopyranoside (9) with 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl trichloroacetimidate (8) gave the (1-3)-linked disaccharide (10), and subsequent benzoylation and deacetylation afforded the disaccharide acceptor 12. Condensation of 12 with 8 yielded methyl 2,3,4-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-3)- alpha-L-rhamnopyranosyl-(1-3)-2,4-di-O-benzoyl-alpha-L- rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-a-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).
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