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Simple Synthesis of Methyl 2-O-β-D-Xylopyranosyl-α-L-arabinofuranoside, a Fragment of Natural Arabinoglucuronoxylans

J. Hirsch and M. Koóš

Institute of Chemistry, Slovak Academy of Sciences, SK-845 38 Bratislava

 

E-mail: chemhirs@savba.sk

Received: 27 October 2003

Abstract: Methyl 3,5-di-O-benzoyl-α-L-arabinofuranoside, prepared by a five-step synthesis from Larabinose, was condensed with 2,3,4-tri-O-acetyl-α-D-xylopyranosyl bromide under modified Koenigs—Knorr conditions using mercuric cyanide as a catalyst and acid scavenger in dichloromethane, giving a high yield (77 %) of the O-protected disaccharide VIII. Removal of acyl groups afforded the desired model compound – methyl 2-O-β-D-xylopyranosyl-α-L-arabinofuranoside. 1H and 13C NMR spectra of the synthesized compounds are also presented.

Full paper in Portable Document Format: 591a21.pdf

 

Chemical Papers 59 (1) 21–24 (2005)

Friday, August 14, 2020

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