| Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN). | |
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MedLine Citation:
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PMID: 22070804 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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Reaction of propargylmagnesium bromide with 2,3;5,6-di-O-isopropylidene-D-mannonolactone followed by highly stereoselective reduction of the so-formed lactol with sodium borohydride gives a syn-diol from which practical syntheses of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN) and various partially protected derivatives have been achieved all of which feature the oxidative unmasking of the α-keto acid moiety from the alkyne. |
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Authors:
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David Crich; Chandrasekhar Navuluri |
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Publication Detail:
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Type: Journal Article; Research Support, N.I.H., Extramural Date: 2011-11-09 |
Journal Detail:
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Title: Organic letters Volume: 13 ISSN: 1523-7052 ISO Abbreviation: Org. Lett. Publication Date: 2011 Dec |
Date Detail:
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Created Date: 2011-11-28 Completed Date: 2012-02-08 Revised Date: 2013-05-23 |
Medline Journal Info:
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Nlm Unique ID: 100890393 Medline TA: Org Lett Country: United States |
Other Details:
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Languages: eng Pagination: 6288-91 Citation Subset: IM |
Affiliation:
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Department of Chemistry, Wayne State University, 5101 Cass Avenue, Detroit, Michigan 48202, USA. DCrich@chem.wayne.edu |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Catalysis Molecular Structure Oxidation-Reduction Stereoisomerism Sugar Acids / chemical synthesis*, chemistry |
| Grant Support | |
ID/Acronym/Agency:
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GM 62160/GM/NIGMS NIH HHS; R01 GM062160-11/GM/NIGMS NIH HHS |
| Chemical | |
Reg. No./Substance:
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0/Sugar Acids; 22594-61-2/3-deoxyglycero-galacto-nonulosonic acid |
| Comments/Corrections | |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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