Regio- and Stereoselective Synthesis of beta-D-Gluco-, alpha-L-Ido-, and alpha-L-Altropyranosiduronic Acids from Delta(4)-Uronates.

@article{Bazin1999RegioAS,
  title={Regio- and Stereoselective Synthesis of beta-D-Gluco-, alpha-L-Ido-, and alpha-L-Altropyranosiduronic Acids from Delta(4)-Uronates.},
  author={H{\'e}l{\`e}ne G. Bazin and Michael Werner Wolff and Robert J. Linhardt},
  journal={The Journal of organic chemistry},
  year={1999},
  volume={64 1},
  pages={144-152}
}
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… CONTINUE READING