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dc.contributor.authorBazin, H.G.
dc.contributor.authorWolff, M.W.
dc.contributor.authorLinhardt, Robert J.
dc.date1999
dc.date.accessioned2022-06-27T16:21:51Z
dc.date.available2022-06-27T16:21:51Z
dc.date.issued1999
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.identifier.urihttps://doi.org/10.1021/jo981477k
dc.identifier.urihttps://hdl.handle.net/20.500.13015/5887
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.description.urihttps://login.libproxy.rpi.edu/login?url=https://doi.org/10.1021/jo981477k
dc.languageen_US
dc.language.isoENG
dc.relation.ispartofThe Linhardt Research Labs Online Collection
dc.relation.ispartofRensselaer Polytechnic Institute, Troy, NY
dc.relation.urihttps://harc.rpi.edu/
dc.subjectBiology
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
dc.typeArticle
dcterms.accessRightshttps://login.libproxy.rpi.edu/login?url=https://doi.org/10.1021/jo981477k
dc.rights.holderIn Copyright : this Item is protected by copyright and/or related rights. You are free to use this Item in any way that is permitted by the copyright and related rights legislation that applies to your use. For other uses you need to obtain permission from the rights-holder(s). https://rightsstatements.org/page/InC/1.0/
dc.creator.identifierhttps://orcid.org/0000-0003-2219-5833
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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