Imino-C-nucleoside Synthesis:  Heteroaryl Lithium Carbanion Additions to a Carbohydrate Cyclic Imine and Nitrone

Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently...

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Bibliographic Details
Published in:Journal of organic chemistry 2004-03, Vol.69 (6), p.2217-2220
Main Authors: Evans, Gary B, Furneaux, Richard H, Hausler, Herwig, Larsen, Janus S, Tyler, Peter C
Format: Article
Language:English
Subjects:
Acetonitriles - chemistry
Anisoles - chemistry
Carbohydrates - chemistry
Carbohydrates. Nucleosides and nucleotides
Chemistry
Ethers - chemistry
Exact sciences and technology
Heterocyclic Compounds - chemical synthesis
Imines - chemistry
Lithium - chemistry
Magnetic Resonance Spectroscopy
Nitrogen Oxides - chemistry
Nucleosides - chemical synthesis
Nucleosides, nucleotides and oligonucleotides
Organic chemistry
Organometallic Compounds - chemistry
Preparations and properties
Temperature
Tin Compounds
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Summary:Promotion by Lewis acid of the addition of some aryllithiums to a carbohydrate-based imine, which has allowed a more facile synthesis of some imino-C-nucleoside analogues, is described. Use of the corresponding nitrone does not assist in some cases, but lithiated acetonitrile adds to it efficiently to give a product from which further C-nucleoside analogues can be derived.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo035744k