Hydrogenolysis of 3,5-0-benzylidene acetals with the LiAlH4-AlCl3 reagent in methyl d-xylofuranosides

András Lipták, András Neszmélyi, Pavol Kováč, Ján Hirsch

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Abstract

The hydrogenolysis of methyl 3,5-0-benzylidene-α- and -β-D-xylofuranoside derivatives with the LiAlH4-AlCl3 reagent gave 5-benzyl ethers as main products. In some cases the attack of the reagent occured at the ring oxygen of the furenoside skeleton to yield 5-0-benzyl-1-0-methylxylitol derivatives. The structure of the synthesized compounds was proved by 13C-NMR spectroscopy. Unambiguous assignment of lines in the 13C-NMR spectra of numerous partially methylated methyl α-and β-d-xylofuranoside derivatives has been made.

Original languageEnglish
Pages (from-to)2379-2382
Number of pages4
JournalTetrahedron
Volume37
Issue number13
DOIs
Publication statusPublished - 1981

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ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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