Fluorous (trimethylsilyl)ethanol: a new reagent for carboxylic acid tagging and protection in peptide synthesis

J Org Chem. 2006 Apr 14;71(8):3299-302. doi: 10.1021/jo052569u.

Abstract

Starting with a fluorous analogue of 2-(trimethylsilyl)ethanol, we have designed an easy method for preparing a new fluorous tag ((F)TMSE) for the protection of carboxylic acids. Because mild conditions are employed in the tag cleavage (TBAF in the presence of 4 A molecular sieves, which prevent racemization), this tag can be advantageously used in the synthesis of peptides and modified peptides, as we have demonstrated with several examples, including the fluorous synthesis of short alpha- and beta-peptides as well as of modified fluorinated retropeptides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carboxylic Acids / chemistry*
  • Molecular Structure
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Trimethylsilyl Compounds / chemistry*

Substances

  • Carboxylic Acids
  • Peptides
  • Trimethylsilyl Compounds