Document Detail


Practical synthesis of 2-keto-3-deoxy-D-glycero-D-galactononulosonic acid (KDN).
MedLine Citation:
PMID:  22070804     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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.
Authors:
David Crich; Chandrasekhar Navuluri
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Publication Detail:
Type:  Journal Article; Research Support, N.I.H., Extramural     Date:  2011-11-09
Journal Detail:
Title:  Organic letters     Volume:  13     ISSN:  1523-7052     ISO Abbreviation:  Org. Lett.     Publication Date:  2011 Dec 
Date Detail:
Created Date:  2011-11-28     Completed Date:  2012-02-08     Revised Date:  2014-09-16    
Medline Journal Info:
Nlm Unique ID:  100890393     Medline TA:  Org Lett     Country:  United States    
Other Details:
Languages:  eng     Pagination:  6288-91     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Catalysis
Molecular Structure
Oxidation-Reduction
Stereoisomerism
Sugar Acids / chemical synthesis*,  chemistry
Grant Support
ID/Acronym/Agency:
GM 62160/GM/NIGMS NIH HHS; R01 GM062160/GM/NIGMS NIH HHS; R01 GM062160-11/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
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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