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

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

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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
Volume70
Issue number18
DOIs
StatePublished - Sep 2 2005

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Nucleosides
Nucleic Acids
Methanol
Derivatives
Heating
Cytidine
Adenosine
Oils
Contamination
Acids
Temperature

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Nucleic acid related compounds. 127. Selective N-deacylation of N,O-peracylated nucleosides in superheated methanol. / Nowak, Ireneusz; Conda-Sheridan, Martin; Robins, Morris J.

In: Journal of Organic Chemistry, Vol. 70, No. 18, 02.09.2005, p. 7455-7458.

Research output: Contribution to journalArticle

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