Regioselective synthesis of substituted 1-thiohex-2-enopyranosides

@article{Dunkerton1988RegioselectiveSO,
  title={Regioselective synthesis of substituted 1-thiohex-2-enopyranosides},
  author={L. Dunkerton and N. Adair and J. M. Euske and K. Brady and P. D. Robinson},
  journal={Journal of Organic Chemistry},
  year={1988},
  volume={53},
  pages={845-850}
}
A variety of 1-thiohex-2-enopyranosides have been prepared from their corresponding 3-O-methyl- or 3-O-acetylglycals by using trimethylsilyl thiols catalyzed by BF/sub 3/ etherate. This method is regioselective for thiolation at C-1 in contrast to the same reaction with thiols which produces C-3 products under thermodynamic control. The stereoselectivity of the reaction depended on the choice of trimethylsily thiol and the leaving group at C-3 of the glycal. ((Trimethylsilyl)thio)benzene gave… Expand
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