| Regio- and Stereoselective Synthesis of beta-D-Gluco-, alpha-L-Ido-, and alpha-L-Altropyranosiduronic Acids from Delta(4)-Uronates. | |
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MedLine Citation:
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PMID: 11674096 Owner: NLM Status: Publisher |
Abstract/OtherAbstract:
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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. |
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Authors:
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Hélène G. Bazin; Michael W. Wolff; Robert J. Linhardt |
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Publication Detail:
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Type: JOURNAL ARTICLE |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 64 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 1999 Jan |
Date Detail:
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Created Date: 2001-Oct-24 Completed Date: - Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: - |
Other Details:
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Languages: ENG Pagination: 144-152 Citation Subset: - |
Affiliation:
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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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From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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