An Alkanesulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis

@article{Backes1999AnA,
  title={An Alkanesulfonamide “Safety-Catch” Linker for Solid-Phase Synthesis},
  author={B. J. Backes and J. Ellman},
  journal={Journal of Organic Chemistry},
  year={1999},
  volume={64},
  pages={2322-2330}
}
An alkanesulfonamide “safety-catch” linker has been developed for tethering carboxylic acids to support. Acylation of the sulfonamide support provides a support-bound N-acylsulfonamide that is stable to both basic and strongly nucleophilic reaction conditions. At the end of a solid-phase synthesis sequence, treatment with iodoacetonitrile provides N-cyanomethyl derivatives that can be cleaved by nucleophiles under mild reaction conditions to release the target compounds. Coupling conditions… Expand
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