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Issue 4, 1989
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On the reaction of 4,6-O-benzylidene-2-deoxypyranosides with sodium cyanoborohydride: formation of 1,5-anhydroalditols

Abstract

Some methyl 4,6-O-benzylidene-2-deoxypyranosides were submitted to the action of sodium cyanoborohydride in acidic medium. Regiospecific cleavage of the benzylidene ring was observed, giving the expected 6-O-benzyl derivative. Depending upon the substitution at C-2 reductive cleavage of the aglycone was observed as a side-reaction or as a main reaction. This could provide a new entry to 1,5-anhydroalditols branched at C-2.

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Article information


J. Chem. Soc., Perkin Trans. 1, 1989, 703-705
Article type
Paper

On the reaction of 4,6-O-benzylidene-2-deoxypyranosides with sodium cyanoborohydride: formation of 1,5-anhydroalditols

Y. Chapleur, P. Boquel and F. Chrétien, J. Chem. Soc., Perkin Trans. 1, 1989, 703 DOI: 10.1039/P19890000703

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