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

Synthesis of 2,4-di-O-β-D-xylopyranosyl-D-xylopyranose

E. Petráková and P. Kováč

Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava

Abstract: Benzylation of benzyl 2,3-anhydro-4-O-β-D-xylopyranosyl-β-D-ribopyranoside followed by nucleophilic opening of the anhydro ring in the fully substituted product with benzyl alcoholate anion in PhCH₂OH gave benzyl 3,2',3',4'-tetra-O-benzyl-β-xylobioside. Treatment of the latter in MeCN with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide in the presence of Hg(CN)₂ afforded the β-linked trisaccharide as the main products (α:β = 2:7). Subsequent removal of blocking groups by catalytic hydrogenolysis yielded the title oligosaccharide. ¹³C-NMR spectra of the title trisaccharide and its 2-O-α-D-xylopyranosyl isomer are presented.

Full paper in Portable Document Format: 355a699.pdf

Chemical Papers 35 (5) 699–705 (1981)