Issue 0, 1984

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1984, 2371-2374

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, 2371 DOI: 10.1039/P19840002371

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