Synthesis of benzyl and benzyloxycarbonyl base-blocked 2'-deoxyribonucleosides

Synthesis of benzyl and benzyloxycarbonyl base-blocked 2'-deoxyribonucleosides

Acylimidazoles have been alkylated with trialkyloxonium tetrafluoroborates to form acylimidazolium salts. The salts, particularly (benzyloxycarbonyl)imidazolium salts, are shown to be effective agents for the direct, mono-N-protection of deoxynucleosides as their acyl derivatives.

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Bibliographische Detailangaben
Veröffentlicht in:J. Org. Chem.; (United States) 1982-11, Vol.47 (23), p.4471-4477
Hauptverfasser: Watkins, Bruce E, Rapoport, Henry
Format: Artikel
Sprache:eng
Schlagworte:
400301 - Organic Chemistry- Chemical & Physicochemical Properties- (-1987)
ALKYLATION
AZOLES
CARBONYLS
CHEMICAL PREPARATION
CHEMICAL PROPERTIES
CHEMICAL REACTIONS
HETEROCYCLIC COMPOUNDS
IMIDAZOLES
INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY
NUCLEOSIDES
NUCLEOTIDES
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
RIBOSIDES
STEREOCHEMISTRY
SYNTHESIS
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Zusammenfassung:Acylimidazoles have been alkylated with trialkyloxonium tetrafluoroborates to form acylimidazolium salts. The salts, particularly (benzyloxycarbonyl)imidazolium salts, are shown to be effective agents for the direct, mono-N-protection of deoxynucleosides as their acyl derivatives.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo00144a014