Biology; Chemistry and chemical biology; Chemical and biological engineering; Biomedical engineering
In 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/;
Regio- 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.
The 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.;
Journal of Organic Chemistry, 64, 144-152; Note : 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.
The Linhardt Research Labs.; The Shirley Ann Jackson, Ph.D. Center for Biotechnology and Interdisciplinary Studies (CBIS);
The Linhardt Research Labs Online Collection; Rensselaer Polytechnic Institute, Troy, NY; https://harc.rpi.edu/;