An In-Depth Study on Ring-Closing Metathesis of Carbohydrate-Derived α-Alkoxyacrylates:  Efficient Syntheses of DAH, KDO, and 2-Deoxy-β-KDO

Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether...

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Bibliographic Details
Published in:Journal of organic chemistry 2006-08, Vol.71 (17), p.6444-6450
Main Authors: Hekking, Koen F. W, Moelands, Marcel A. H, van Delft, Floris L, Rutjes, Floris P. J. T
Format: Article
Language:English
Subjects:
Acrylates - chemistry
Alkylation
Carbohydrates - chemistry
Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides
Carbohydrates. Nucleosides and nucleotides
Catalysis
Chemistry
Exact sciences and technology
Isomerism
Molecular Structure
Organic chemistry
Oxygen - chemistry
Preparations and properties
Sugar Acids - chemical synthesis
Sugar Acids - chemistry
Sugar Phosphates - chemical synthesis
Sugar Phosphates - chemistry
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Summary:Novel, efficient synthetic pathways to DAH, KDO, and 2-deoxy-β-KDO are described. Ring-closing metathesis (RCM) of highly functionalized α-alkoxyacrylate fragments resulted in a series of synthetically versatile oxygen heterocyclic intermediates. Further functionalization of the resulting enol ether double bond and subsequent deprotection provided the natural products in high overall yields, starting from commercially available protected sugars.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo060913x