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Synthesis 1985; 1985(12): 1123-1125
DOI: 10.1055/s-1985-31447
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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
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Publication Date:
27 September 2002 (online)

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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 1 to afford the deprotected species 2. Glycosides and acetals are unaffected by the treatment.