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dc.contributor.authorBazin, H.G.
dc.contributor.authorWolff, M.W.
dc.contributor.authorLinhardt, Robert J.
dc.identifier.citationRegio- and Stereoselective Synthesis of b-D-Gluco-, a -L-Ido-and a -L-Altro pyranosiduronicAcids from D 4-Uronates, H. G. Bazin,M.W. Wolff, R.J. Linhardt, Journal of Organic Chemistry, 64,144-152, 1999.
dc.descriptionJournal of Organic Chemistry, 64, 144-152
dc.descriptionNote : if this item contains full text it may be a preprint, author manuscript, or a Gold OA copy that permits redistribution with a license such as CC BY. The final version is available through the publisher’s platform.
dc.description.abstractThe stereoselective synthesis of B-D-glucopyranosiduronic, R-L-idopyranosiduronic, and R-L-altro-pyranosiduronic acids has been performed from different ∆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 R-L C-4 ketopyranosides adopting the 1C4 chair conformation. Hydride reduction afforded the R-L-idopyranosiduronic or the R-L-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
dc.relation.ispartofThe Linhardt Research Labs Online Collection
dc.relation.ispartofRensselaer Polytechnic Institute, Troy, NY
dc.subjectChemistry and chemical biology
dc.subjectChemical and biological engineering
dc.subjectBiomedical engineering
dc.titleRegio- and Stereoselective Synthesis of b-D-Gluco-, a -L-Ido-and a -L-Altro pyranosiduronicAcids from D 4-Uronates
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dc.relation.departmentThe Linhardt Research Labs.
dc.relation.departmentThe Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS)

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