Document Detail


Two-step synthesis of carbohydrates by selective aldol reactions.
MedLine Citation:
PMID:  15308765     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Studies of carbohydrates have been hampered by the lack of chemical strategies for the expeditious construction and coupling of differentially protected monosaccharides. Here, a synthetic route based on aldol coupling of three aldehydes is presented for the de novo production of polyol differentiated hexoses in only two chemical steps. The dimerization of alpha-oxyaldehydes, catalyzed by l-proline, is then followed by a tandem Mukaiyama aldol addition-cyclization step catalyzed by a Lewis acid. Differentially protected glucose, allose, and mannose stereoisomers can each be selected, in high yield and stereochemical purity, simply by changing the solvent and Lewis acid used. The reaction sequence also efficiently produces (13)C-labeled analogs, as well as structural variants such as 2-amino- and 2-thio-substituted derivatives.
Authors:
Alan B Northrup; David W C MacMillan
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S.; Research Support, U.S. Gov't, P.H.S.     Date:  2004-08-12
Journal Detail:
Title:  Science (New York, N.Y.)     Volume:  305     ISSN:  1095-9203     ISO Abbreviation:  Science     Publication Date:  2004 Sep 
Date Detail:
Created Date:  2004-09-17     Completed Date:  2004-09-24     Revised Date:  2007-11-14    
Medline Journal Info:
Nlm Unique ID:  0404511     Medline TA:  Science     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1752-5     Citation Subset:  IM    
Affiliation:
Department of Chemistry, California Institute of Technology, 1200 East California Boulevard, Pasadena, CA 91125, USA.
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MeSH Terms
Descriptor/Qualifier:
Acids
Aldehydes / chemistry
Carbon Isotopes
Catalysis
Cyclization
Dimerization
Hexoses / chemical synthesis*,  chemistry,  isolation & purification
Molecular Conformation
Molecular Structure
Proline / chemistry*
Solvents
Stereoisomerism
Grant Support
ID/Acronym/Agency:
R01 GM66142-01/GM/NIGMS NIH HHS
Chemical
Reg. No./Substance:
0/Acids; 0/Aldehydes; 0/Carbon Isotopes; 0/Hexoses; 0/Solvents; 107-89-1/3-hydroxybutanal; 147-85-3/Proline
Comments/Corrections
Comment In:
Science. 2004 Sep 17;305(5691):1725-6   [PMID:  15375255 ]

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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