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Alternative syntheses of methylated sugars. XVIII. Synthesis of methyl 2,4-di-O-acetyl-β-D-xylopyranoside

P. Kováč and J. Alföldi

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

 

Abstract: Me 2,4-di-O-acetyl-3-O-benzyl-β-D-xylopyranoside (I), from which the title glycoside can be obtained in a virtually quant. yield, was prepd. via independent routes. In the 1st procedure, 3-O-benzyl-D-xylose was acetylated with Ac2O in pyridine under controlled conditions to give 85% of cryst. 1,2,4-tri-O-acetyl-3-O-benzyl-α,β-D-xylopyranose (II). Treatment of II with HBr in CH2Cl2 gave the corresponding glycosyl halide and I was obtained by condensation of the halide with MeOH in the presence of Hg(CN)2. The alternative procedure for the prepn. of I comprises opening of the anhydro ring in Me 2,3-anhydro-β-D-ribopyranoside with benzyl alcoholate anion in PhCH2OH and conventional acetylation of the formed Me 3-O-benzyl-β-D-xylopyranoside.

Full paper in Portable Document Format: 336a785.pdf

 

Chemical Papers 33 (6) 785–791 (1979)

Monday, October 14, 2019

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