| Stereoselective access to the versatile 4-aminohex-5-ene-1,2,3-triol pattern. | |
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MedLine Citation:
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PMID: 15575756 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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We developed a stereocontrolled route allowing potential access to the eight isomers of 4-benzylaminohex-5-ene-1,2,3-triol in two or four steps and ca. 50% yield from readily available chiral nonracemic cis- or trans-alpha,beta-epoxyimine precursors. A new (NH(4))(2)CO(3)-based carboxylation/intramolecular cyclization sequence allowed regio- and stereocontrolled C-3 epoxide opening while neat C-2 hydrolysis was ensured by simple aqueous acidic treatment. |
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Authors:
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Tahar Ayad; Vanessa Faugeroux; Yves Génisson; Chantal André; Michel Baltas; Liliane Gorrichon |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 69 ISSN: 0022-3263 ISO Abbreviation: J. Org. Chem. Publication Date: 2004 Dec |
Date Detail:
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Created Date: 2004-12-03 Completed Date: 2005-02-14 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 8775-9 Citation Subset: IM |
Affiliation:
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Laboratoire Synthèse et Physicochimie des Molécules d'Intéret Biologique, UMR 5068 CNRS, Université Paul Sabatier, 118 route de Narbonne, 31062 Toulouse Cedex 04, France. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cyclization Epoxy Compounds / chemical synthesis, chemistry Hexanols / chemical synthesis* Hydrolysis Molecular Conformation Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/4-aminohex-5-ene-1,2,3-triol; 0/Epoxy Compounds; 0/Hexanols |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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