10.6084/m9.figshare.4772284.v1
Mohindra Seepersaud
Mohindra
Seepersaud
Savita Seecharan
Savita
Seecharan
Lorale J. Lalgee
Lorale J.
Lalgee
Nigel Kevin Jalsa
Nigel Kevin
Jalsa
Ceric ammonium nitrate/acetic anhydride: A tunable system for the <i>O</i>-acetylation and mononitration of diversely protected carbohydrates
Taylor & Francis Group
2017
Acetylation
carbohydrates
ceric ammonium nitrate
nitration
protecting groups
2017-03-21 16:42:54
Journal contribution
https://tandf.figshare.com/articles/journal_contribution/Ceric_ammonium_nitrate_acetic_anhydride_A_tunable_system_for_the_i_O_i_-acetylation_and_mononitration_of_diversely_protected_carbohydrates/4772284
<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>