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Stereoselective synthesis and 13C NMR spectra of lower oligosaccharides related to arabinoxylan

J. Hirsch, E. Petráková, and M. Hricovíni

Institute of Chemistry, Centre for Chemical Research, Slovak Academy of Sciences, CS-84238 Bratislava

 

Abstract: Nucleophiles — l,2,4-tri-0-acetyl- β-D-xylopyranose, methyl 2,4-di-O-acetyl-β-D-xylopyranoside, methyl 3,4-di-0-benzyl-β-D-xylopyranoside, and methyl 4-0-benzyl-β-D-xylopyranoside — were separately condensed with 2,3,5-tri-O-benzoyl-α-L-arabinofuranosyl bromide under modified Koenigs—Knorr conditions giving high yields ( ≈90%) of substituted disaccharides and trisaccharide, respectively. Removal of the protecting groups afforded 3-O-α-L-arabinofuranosyl-D-xylopyranose, methyl 3-O-α-L-arabinofuranosyl-β-D-xylopyranoside, methyl 2-0-α-L-arabinofuranosyl-β-D-xylopyranoside, and methyl 2,3-di-0-(α-L-arabinofuranosyl)-ß-D-xylopyranoside. 13C NMR spectra of the synthesized compounds are also presented.

Full paper in Portable Document Format: 433a395.pdf

 

Chemical Papers 43 (3) 395–402 (1989)

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