Solid-supported hydrazone of 4-(4'-formyl-3'-methoxyphenoxy)butyric acid as a new traceless linker for solid-phase synthesis

Org Lett. 2015 Jan 16;17(2):180-3. doi: 10.1021/ol5034223. Epub 2014 Dec 23.

Abstract

The use of a hydrazine derived from a backbone amide linker as a new hydrazone-based traceless linker for solid-phase organic synthesis is described. The stability of the linker was tested under various conditions, including treatment with acids, bases, and borohydrides. Final compounds can be released by selective cleavage using trimethylsilanolate. To demonstrate the versatility of the linker, the synthesis of a model compound under various reaction conditions was performed with good results.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butyrates / chemical synthesis*
  • Butyrates / chemistry
  • Combinatorial Chemistry Techniques
  • Hydrazones / chemistry*
  • Molecular Structure
  • Solid-Phase Synthesis Techniques

Substances

  • 4-(4'-formyl-3'-methoxyphenoxy)butyric acid
  • Butyrates
  • Hydrazones