ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)