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Sequential synthesis and  13C NMR spectra of methyl 3-O- and 2-O-(β-D-xylobiosyl)-β-D-xylopyranosides

J. Hirsch and E. Petráková

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-842 38 Bratislava


Abstract: Condensation of 2,3-di-O-acetyl-4-O-benzyl-α,β-D-xylopyranosyl bromide with Me 2,4-di-O-acetyl-β-D-xylopyranoside yielded a mixt. of Me tetra-O-acetyl-4'-O-benzyl-α- and -β-(1→3)-D-xylobiosides. From the latter the disaccharide I having a free hydroxyl group at C-4' was isolated by chromatog. after debenzylation. Then it was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide. The resulting peracetylated trisaccharides isomeric in the site of the interglycosidic linkage of the nonreducing end yielded after deacetylation the title Me 3-O-(β-D-xylobiosyl)-β-D-xylopyranoside and its 4'-O-α-glycosidically bound isomer. The same synthetic principle was applied to the synthesis of Me 2-O-(β-D-xylobiosyl)-β-D-xylopyranoside using Me 3,4-di-O-acetyl-β-D-xylopyranoside as a nucleophile. All the compds. reported were obtained in cryst. state. Their 13C NMR spectra are also presented and interpreted.

Full paper in Portable Document Format: 383a409.pdf


Chemical Papers 38 (3) 409–417 (1984)

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