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

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

doi:10.1021/jo051256w

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 journal › Article › peer-review

12 Scopus citations

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 language	English (US)
Pages (from-to)	7455-7458
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	70
Issue number	18
DOIs	https://doi.org/10.1021/jo051256w
State	Published - Sep 2 2005
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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10.1021/jo051256w

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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.",

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AU - Robins, Morris J.

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Y1 - 2005/9/2

N2 - 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.

AB - 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.

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

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