BORANE-AMINE COMPLEXES - VERSATILE REAGENTS IN THE CHEMISTRY OF NUCLEIC ACIDS AND THEIR ANALOGS

A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4′-dimet...

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Bibliographic Details
Published in:Nucleosides, nucleotides & nucleic acids nucleotides & nucleic acids, 2001-04, Vol.20 (4-7), p.941-945
Main Authors: Sergueeva, Zinaida A., Sergueev, Dmitri S., Shaw, Barbara Ramsay
Format: Article
Language:English
Subjects:
Alkylation
Amines - chemistry
Boranes - chemistry
Nucleosides - chemical synthesis
Reducing Agents - chemistry
Trityl Compounds - chemistry
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Summary:A new method for synthesis of N-alkylated nucleosides was developed. Exceptionally mild and selective conversion of N-acyl to the corresponding N-alkyl nucleosides was achieved by reduction with borane-amine complexes. The borane-amine complexes were also used as efficient scavengers of a 4,4′-dimethoxytrityl (DMT) cation. Neutralization of the cation eliminated the boranophosphate group degradation during acidic DMT deprotection and allowed milder acidic conditions for the deprotection.
ISSN:1525-7770
1532-2335
DOI:10.1081/NCN-100002464