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Mild Deprotection of Benzyl Ether Protective Groups with Ozone

Pierre Angibeaud*, Jacques Defaye, Andrée Gadelle, Jean-Pierre Utille

*Centre de Recherches sur les Macromolécules Végétales, Centre National de la Recherche Scientifique, Grenoble, B. P. 68, F-38402-Saint Martin d'Hères, France

P. Angibeaud, J. Defaye, A. Gadelle, J.-P. Utille, Synthesis, 1985, 1123-1125.

DOI: 10.1055/s-1985-31447


Benzyl ether protective groups are oxidatively removed by ozone under relatively mild conditions. Reaction products are benzoic ester, benzoic acid, and the corresponding alcohol. Subsequent deacylation with sodium methoxide affords a convenient debenzylation technique which has been applied to various O-benzyl protected carbohydrates.

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Key Words

benzyl ethers, Ozone

ID: J60-Y1985-160