Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol

Ireneusz Nowak, Martin Conda-Sheridan, Morris J. Robins

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Solutions of peracylated adenosine, cytidine, and related nucleoside derivatives undergo selective N-deacylation upon heating at elevated temperatures (oil bath ≥ 105 °C) in methanol. An increase in the bulk of the N-acyl group has little effect on the rate of N-deacylation but increases the N/O selectivity ratio. Extended heating is required for N-deacylation with arylcarboxylic acid derivatives. Contamination with acidic or basic reagent residues is avoided.

Original languageEnglish (US)
Pages (from-to)7455-7458
Number of pages4
JournalJournal of Organic Chemistry
Issue number18
Publication statusPublished - Sep 2 2005


ASJC Scopus subject areas

  • Organic Chemistry

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