Ceric ammonium nitrate/acetic anhydride: A tunable system for the <i>O</i>-acetylation and mononitration of diversely protected carbohydrates

<p>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 <i>O</i>-acetylated products, their mononitrated counterparts were also produced depending upon the reactivity of the starting material. Decreasing the molar equivalents of CAN afforded the <i>O</i>-acetylated products exclusively, while increasing it favored the mononitrated derivatives.</p>