Syntheses of P-Nitrophenyl 6-O-α- and 6-O-β-D-Xylopyranosyl-β-D-glucopyranoside

6 December 1986

journal article
research article
Published by Taylor & Francis in Journal of Carbohydrate Chemistry

Vol. 5 (4) , 671-682
https://doi.org/10.1080/07328308608062983

Abstract

Condensation of p-nitrophenyl 2,3,4-tri-O-benzoyl-.beta.-D-glucopyranoside 3 with 2,3,4-tri-O-(chlorosulfonyl)-.beta.-D-xylopyranosyl chloride by the Koenigs-Knorr method afforded the .alpha.-linked product in a high yield. Dechlorosulfation with sodium iodide and debenzoylation by the Zemplen method gave crystalline p-nitrophenyl 6-O-(.alpha.-D-xylopyranosyl)-.beta.-D-glucopyranoside 7. Compound 3 was condensed with 2,3,4-tri-O-benzoyl-.alpha.-D-xylopyranosyl bromide in the presence of mercury (II) cyanide in acetonitrile, and after debenzoylation, crystalline p-nitrophenyl 6-O-(.beta.-D-xylopyranosyl)-.beta.-D-glucopyranoside 10 was obtained.

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