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Issue 0, 1984
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Regioselective reductive ring-opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protecting-group strategy. Part 1

Abstract

Reduction of fully protected 4,6-O-(4-methoxybenzylidene) hexopyranosides with sodium cyanoboro-hydride–trifluoroacetic acid in NN′-dimethylformamide, or trimethylsilyl chloride in acetonitrile, gives the 6- and 4-O-(4-methoxybenzyl) ethers, respectively, in good yield and good regioselectivity. The 4-methoxybenzyl ether linkage in products containing benzyl ethers or other protective groups is selectively cleaved upon treatment with cerium(IV) ammonium nitrate in aqueous acetonitrile.

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Article type: Paper
DOI: 10.1039/P19840002371
Citation: J. Chem. Soc., Perkin Trans. 1, 1984,0, 2371-2374
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    Regioselective reductive ring-opening of 4-methoxybenzylidene acetals of hexopyranosides. Access to a novel protecting-group strategy. Part 1

    R. Johansson and B. Samuelsson, J. Chem. Soc., Perkin Trans. 1, 1984, 0, 2371
    DOI: 10.1039/P19840002371

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