Rapid and Selective Reduction of Amide Group by Borane-Amine Complexes in Acyl Protected Nucleosides

Rapid and Selective Reduction of Amide Group by Borane-Amine Complexes in Acyl Protected Nucleosides

Borane-amine complexes provide an unusually fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nuc...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids Vol. 19; no. 1-2; pp. 275 - 282
Main Authors: Sergueeva, Zinaida A., Sergueev, Dmitri S., Shaw, Barbara Ramsay
Format: Journal Article
Language:English
Published: United States Taylor & Francis Group 01-01-2000
Subjects:
Amides - chemistry
Amines - chemistry
Boranes - chemistry
Chromatography, High Pressure Liquid
Magnetic Resonance Spectroscopy
Nucleosides - chemistry
Oxidation-Reduction
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Summary:Borane-amine complexes provide an unusually fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.
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ISSN:1525-7770
1532-2335
DOI:10.1080/15257770008033009