Regio and Stereoselective Synthesis of Derivatives of L-Idopyranuronic Acid and D-Glucopyranuronic Acid from D4-Uronates
No Thumbnail Available
Authors
Bazin, H.G.
Kerns, R.J.
Linhardt, Robert J.
Issue Date
1997
Type
Article
Language
ENG
Keywords
Biology , Chemistry and chemical biology , Chemical and biological engineering , Biomedical engineering
Alternative Title
Abstract
The stereoselective synthesis of β-d-glucopyranosiduronic, α-l-idopyranosiduronic, and α-l-altropyranosiduronic acids has been performed from different Δ4-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 α-l C-4 ketopyranosides adopting the 1C4 chair conformation. Hydride reduction afforded the α-l-idopyranosiduronic or the α-l-altropyranosiduronic acids, the stereoselectivity of the reduction being controlled by the appropriate substitution pattern.
Description
Tetrahedron Letters, 38, 923-926
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.
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.
Full Citation
Regio and Stereoselective Synthesis of Derivatives of L-IdopyranuronicAcid and D-Glucopyranuronic Acid from D4-Uronates, H. G. Bazin, R.J. Kerns,R.J. Linhardt, Tetrahedron Letters, 38, 923-926, 1997.