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Regio- and Stereoselective Synthesis of beta-D-Gluco-, alpha-L-Ido-, and alpha-L-Altropyranosiduronic Acids from Delta(4)-Uronates.
MedLine Citation:
PMID:  11674096     Owner:  NLM     Status:  Publisher    
Abstract/OtherAbstract:
The stereoselective synthesis of beta-D-glucopyranosiduronic, alpha-L-idopyranosiduronic, and alpha-L-altropyranosiduronic acids has been performed from different Delta(4)-uronate monosaccharides. Bromination of the C-4,5 double bond provided the trans-diaxial bromohydrin derivatives, which were converted to the corresponding epoxides in high yields. Direct reduction of the epoxides using borane-tetrahydrofuran complex led to the corresponding glucuronic acids in low to good yields. Glucuronic acids were also obtained in satisfactory yields through a two-steps procedure involving bromination of the epoxide with titanium(IV) bromide followed by reduction using tributyltin hydride. Lewis acid-catalyzed rearrangement of these epoxides led to the corresponding alpha-L C-4 ketopyranosides adopting the (1)C(4) chair conformation. Hydride reduction afforded the alpha-L-idopyranosiduronic or the alpha-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
Authors:
Hélène G. Bazin; Michael W. Wolff; Robert J. Linhardt
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Publication Detail:
Type:  JOURNAL ARTICLE    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  64     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  1999 Jan 
Date Detail:
Created Date:  2001-Oct-24     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  -    
Other Details:
Languages:  ENG     Pagination:  144-152     Citation Subset:  -    
Affiliation:
Division of Medicinal and Natural Products Chemistry and Department of Chemical and Biochemical Engineering, The University of Iowa, PHAR-S328, Iowa City, Iowa 52242.
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