Convenient Synthesis of Nucleoside and Isonucleoside Analogues

A very simple methodology to stereoselectively achieve tricyclic isonucleosides (nucleobase = thymine, uracil, and 5-fluoruracil) and 3‘-C-branched nucleosides (nucleobase = theophylline) was performed by means of a DBU-mediated addition process using a readily available 2-bromo sugar. The mechanism...

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Bibliographic Details
Published in:Organic letters 2005-05, Vol.7 (11), p.2161-2164
Main Authors: Álvarez de Cienfuegos, Luis, Mota, Antonio J, Robles, Rafael
Format: Article
Language:English
Subjects:
Catalysis
Cytosine - chemistry
Indicators and Reagents
Molecular Structure
Nucleosides - chemical synthesis
Nucleosides - chemistry
Thymine - chemistry
Uracil - chemistry
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Summary:A very simple methodology to stereoselectively achieve tricyclic isonucleosides (nucleobase = thymine, uracil, and 5-fluoruracil) and 3‘-C-branched nucleosides (nucleobase = theophylline) was performed by means of a DBU-mediated addition process using a readily available 2-bromo sugar. The mechanism for these transformations implies the loss of both substituents at C-2 and C-3 on the sugar moiety, and although it seems that DBU is probably involved, its involvement has not yet been ascertained. Cytosine did not react under these conditions.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol050496v