171613-12-0Relevant articles and documents
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
Zhang, Jianjun,Kong, Fanzuo
, p. 89 - 97 (2002)
A xylosylated rhamnose pentasaccharide, α-L-Rhap-(1→3)-[β-L-Xylp-(1→ 2)-] [β-L-Xylp-(1→4)-]α-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-α-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-α-L-rhamnopyranosyl-(1→3)-α-L- rhamnopyranosyl-(1→3)-2,4-di-O-benzoyl-α-L-rhamnopyranoside (13). Coupling of 13 with 2,3,4-tri-O-benzoyl-α-L-xylopyranosyl trichloroacetimidate (4) followed by deprotection gave the target pentasaccharide (15).