Synthesis and Properties of Spiro Nucleosides Containing the Barbituric Acid Moiety

The two chiral spiro nucleosides 4 and 5 containing the barbituric acid moiety were efficiently synthesized from optically pure precursors, and their properties were studied. The carbocyclic nucleoside 5 is considerably more stable against ring opening than the deoxyribosyl derivative 4. Both compou...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-02, Vol.67 (4), p.1302-1307
Main Authors: Renard, Annabelle, Lhomme, Jean, Kotera, Mitsuharu
Format: Article
Language:English
Subjects:
Barbiturates - chemical synthesis
Barbiturates - chemistry
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Chemistry, Organic - methods
Cyclization
Exact sciences and technology
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleosides - chemical synthesis
Nucleosides - chemistry
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Preparations and properties
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
Streptomyces - chemistry
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Summary:The two chiral spiro nucleosides 4 and 5 containing the barbituric acid moiety were efficiently synthesized from optically pure precursors, and their properties were studied. The carbocyclic nucleoside 5 is considerably more stable against ring opening than the deoxyribosyl derivative 4. Both compounds present enhanced hydrogen bonding capacity with diacetyladenosine.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo016194y