Fluorous (Trimethylsilyl)ethanol: A New Reagent for Carboxylic Acid Tagging and Protection in Peptide Synthesis

6533b835fe1ef96bd129f643

RESEARCH PRODUCT

Fluorous (Trimethylsilyl)ethanol: A New Reagent for Carboxylic Acid Tagging and Protection in Peptide Synthesis

Juan F. Sanz-cervera José Luis Aceña Carlos Del Pozo Amador Garcia Sancho Gema Chiva Santos Fustero

subject

chemistry.chemical_classification Trimethylsilyl Compounds Ethanol Molecular Structure Trimethylsilyl Chemistry Carboxylic acid Organic Chemistry Carboxylic Acids Peptide Chemical synthesis chemistry.chemical_compound Reagent Peptide synthesis Organic chemistry Peptides Racemization

description

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.

year	journal	country	edition	language
2006-04-08	The Journal of Organic Chemistry

https://doi.org/10.1021/jo052569u

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