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Hydrothermal Deamidation of 4-N-Acylcytosine Nucleoside Derivatives:  Efficient Synthesis of Uracil Nucleoside Esters

Posted on 2005-10-27 - 00:00
N,O-Peracylated cytidine and 2‘-deoxycytidine derivatives in superheated water/DME solutions (oil bath at 125 °C) undergo hydrolytic deamidation (and/or N-deacylation). Acylated starting materials derived from arylcarboxylic acids give the corresponding uridine esters cleanly, and such derivatives crystallize selectively from the cooled reaction mixtures in high yields.

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