Ceric ammonium nitrate/acetic anhydride: A tunable system for the O-acetylation and mononitration of diversely protected carbohydrates |
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Authors: | Mohindra Seepersaud Savita Seecharan Lorale J Lalgee |
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Institution: | Department of Chemistry, University of the West Indies, St. Augustine, Trinidad and Tobago |
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Abstract: | Esterification of a wide range of partially protected carbohydrate derivatives was achieved using acetic anhydride and a catalytic amount of ceric ammonium nitrate (CAN). Compatibility with the commonly used protecting groups was demonstrated, with the esterified products being furnished in good yields. Apart from affording the O-acetylated products, their mononitrated counterparts were also produced depending upon the reactivity of the starting material. Decreasing the molar equivalents of CAN afforded the O-acetylated products exclusively, while increasing it favored the mononitrated derivatives. |
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Keywords: | Acetylation carbohydrates ceric ammonium nitrate nitration protecting groups |
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