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A facile chemoselective deacetylation in the presence of benzoyl and p-bromobenzoyl groups using p-toluenesulfonic acid

AuthorsGonzález, Antonio G.; Brouard, Ignacio ; León, Francisco ; Padrón, Juan I. ; Bermejo, Jaime
KeywordsHemoselective deacetylation
p-toluenesulfonic acid
Issue Date30-Apr-2001
CitationTetrahedron Letters 42(18): 3187-3188 (2001)
AbstractThe acetyl group was chemoselectively cleaved in the presence of p-toluenesulfonic acid (p-TsOH) in CH2Cl2/MeOH without affecting the benzoyl (benzoate and p-bromobenzoate) groups and no transesterification product was observed. The treatment of protected carbohydrates with p-TsOH·H2O at room temperature usually required a longer reaction time than at 40°C. Other types of sulfonic acid such as 10-camphorsulfonic (CSA) led to similar results.
Publisher version (URL)http://dx.doi.org/10.1016/S0040-4039(01)00406-3
Identifiersdoi: 10.1016/S0040-4039(01)00406-3
issn: 0040-4039
Appears in Collections:(IPNA) Artículos
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