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- W2004952012 abstract "The synthesis of the trisaccharide O-β-l-rhamnopyranosyl-(1→4)-O-β-l-rhamnopyranosyl-(1→2)-l-rhamnopyranose (14) and the tetrasaccharide O-(2-acetamido-2-deoxy-β-d-galactopyranosyl)-(1→2)-O-[β-l-rhamnopyranosyl-(1→4)]-O-β- l-rhamnopyranosyl-(1→2)-l-rhamnopyranose (21) is described. The latter structure has been proposed as the repeating unit of the O-specific side-chain of the lipopolysaccharide obtained from Shigella flexneri Serotype 6. The key-intermediate was 4-O-acetyl-2-O-allyl-3-O-benzyl-α-d-rhamnopyranosyl bromide, which was first linked to benzyl 3,4-di-O-benzyl-α-l-rhamnopyranoside, to give a blocked β-linked disaccharide. This was O-deacetylated and coupled with 2,3,4-tri-O-benzyl-α-l-rhamnopyranosyl bromide at O-4′ to afford benzyl O-(2,3,4-tri-O-benzyl-β-l-rhamnopyranosyl)-(1→4)-O-(2-O-allyl-3-O-benzyl-β-l- rhamnopyranosyl)-(1→2)-3,4-di-O-benzyl-α-l-rhamnopyranoside (11), which was deprotected to give 14. Deallylation of 11 and coupling with 6-O-acetyl-2-azido-3,4-di-O-benzyl-2-deoxy-α-d-galactopyranosyl bromide led to a protected tetrasaccharide from which 21 was obtained. The method of catalysis by silver silicate was employed to obtain the β-glycosidic linkage of all monosaccharide units. Es wird die Synthese des Trisaccharides O-β-l-Rhamnopyranosyl-(1→4)-O-β-l-rhamnopyranosyl-(1→2)-O-l-rhamnopyranose (14) und des Tetrasaccharides O-(2-Acetamido-2-desoxy-β-d-galactopyranosyl)-(1→2)-O-[(β-l-rhamnopyranosyl)-(1→4)]-O-β-l-rhamnopyranosyl-(1→2)- l-rhamnopyranose (21) beschrieben. Die letztere Struktur entspricht der Sequenz, wie sie für die Repeating-unit der O-spezifischen Kette des Lipopolysaccharides aus Shigella flexneri Serotyp 6 vorgeschlagen wurde. Der Schlüsselbaustein ist 4-O-Acetyl-2-O-allyl-3- O-benzyl-α-l-rhamnopyranosylbromid, das zunächst mit Benzyl-3,4-di-O-benzyl-α-l-rhamnopyranosid zu einem blockierten Disaccharid verknüpft wird Entacetylierung und ausschließende Glycosidierung mit 2,3,4-Tri-O-benzyl-α-l-rhamnopyranosylbromid an O-4′liefert Benzyl-O-(2,3,4-tri-O-benzyl-β-l-rhamnopyranosyl-(1→4)-O-(2-O-allyl-3-O-benzyl-β-l-rhamnopyranosyl- (1→2)-3,4-di-O-benzyl-α-l-rhamnopyranosid (11), dessen Entlockierung 14 ergibt. Entallylierung von 11 und Kopplung mit 6-O-Acetyl-2-azido-3,4-di-O-benzyl-2-desoxy-α-d-galactopyranosylbromid führt zu einem blockierter Tetrasaccharid, aus dem man danach 21 erhält. Für die Herstellung der β-glycosidischen Bidung aller Monosaccharid-Einheiten hat sich das Verfahren der Anwendung eines Silbersilikat-Katalysators bestens bewährt." @default.
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- W2004952012 date "1983-08-01" @default.
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- W2004952012 title "Synthese von β-l-rhamnosidisch verknüpften oligosacchariden des lipopolysaccharides aus Shigella flexneri sero-typ 6" @default.
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- W2004952012 doi "https://doi.org/10.1016/0008-6215(83)88004-5" @default.
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