Hydrogenolysis of 3,5-0-benzylidene acetals with the LiAlH4-AlCl3 reagent in methyl d-xylofuranosides |
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| Authors: | András Lipták András Neszmélyi Pavol Kováč Ján Hirsch |
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| Affiliation: | Institute of Biochemistry, L. Kossuth University, H-4010 Debrecen, Hungary;The Central Research Institute of the Hungarian Academy of Sciences, H-1525 Budapest, Hungary;Institute of Chemistry, Slovak Academy of Sciences, 809 33 Bratislava, Czechoslovakia |
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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. |
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