Document Detail

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    
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.
Hélène G. Bazin; Michael W. Wolff; Robert J. Linhardt
Related Documents :
22024166 - Class iii pi-3-kinase activates phospholipase d in an amino acid-sensing mtorc1 pathway.
2926326 - Interferon alpha associated with systemic lupus erythematosus is not intrinsically acid...
19826666 - Brønsted acid activation of alpha-diazo imide: a syn-selective glycolate mannich react...
7623036 - Three new omega-cycloheptyl fatty acids from alicyclobacillus cycloheptanicus and their...
3746446 - Measurement of myocardial fatty acid metabolism: kinetics of iodine-123 heptadecanoic a...
12101296 - Tago is involved in the synthesis of all anionic cell-wall polymers in bacillus subtili...
Publication Detail:
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:  -    
Division of Medicinal and Natural Products Chemistry and Department of Chemical and Biochemical Engineering, The University of Iowa, PHAR-S328, Iowa City, Iowa 52242.
Export Citation:
APA/MLA Format     Download EndNote     Download BibTex
MeSH Terms

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

Previous Document:  Electrolytic Partial Fluorination of Organic Compounds. 31.(1) Regioselective Anodic Fluorination of...
Next Document:  Oximidines I and II: Novel Antitumor Macrolides from Pseudomonas sp.