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Improvements in the synthesis of xylobiose (4-O-β-D-xylopyranosyl-D-xylopyranose)

P. Kováč

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

 

Abstract: Reaction of 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-xylopyranose with benzyl 2,3-anhydro-β-D-ribopyranoside followed by deacetylation gave benzyl 2,3-anhydro-4-O-(β-D-xylopyranosyl)-β-D-ribopyranoside (I) in 62% overall yield. Opening of the anhydro ring in I by alk. hydrolysis and then acetylation yielded cryst. benzyl per-O-acetyl-β-xylobioside; catalytic hydrogenolysis and acetylation than gave xylobiose per-O-acetate. Deacetylation of the β-acetate afforded xylobiose.

Full paper in Portable Document Format: 333a365.pdf

 

Chemical Papers 33 (3) 365–370 (1979)

Wednesday, June 19, 2024

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