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Protecting groups and tags

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Boc-ON  

Silanes

PMB OH

t-Butanol   

Cbz-Osu  

Thiol   

Benzyl alcohol

FluoMar  

Oxybenzaldehyde

Fmoc  

Trityl Chlorides

Trityl Alcohols

Thiophenol

Fluorous tags are perfluoroalkyl modified versions of traditional protecting groups familiar to synthetic organic chemists.  Conceptually they are very similar to solid phase tags, but fluorous tags and fluorous tagged substrates are soluble in most organic solvents, such as DMF, THF, CH2Cl2, etc.  This provides some distinct advantages over solid phase tagging strategies including solution phase kinetics, complete control of reaction stoichiometry, and the ability to monitor reactions easily using traditional analytical techniques, including TLC, NMR, GC, LC/MS, and IR.  The fluorous tagged materials are easily separated from non-tagged components by F-SPE.  Fluorous tags have been used in a variety of total, parallel, and mixture syntheses (1-3).

1. Zhang, W. “Fluorous Protecting Groups and Tags” in Handbook of Fluorous Chemistry Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp222-2362.

2. Zhang, W. “Fluorous Tagging Strategy for Solution-Phase Synthesis of Small Molecules, Peptides and Oligosaccharides” Curr. Opin. Drug Disov. Develop. 2004, 7, 784-797.

3. Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000, p 25-37.

 
 
Thiol
 

 

F-thiol is the solution phase equivalent of polymer-bound thiol and has been used as fluorous tags in parallel synthesis.  F-thiol has also been used as a scavenger for various electrophiles and as deprotecting agent for 2-nitrobenzenesulfonamides.  F017023 has the appropriate fluorine content to be retained on F-SPE cartridges for easy separation.

  1. Zhang, W. Org. Lett., 2003, 5(7), 1011.
  2. FTI Application Note "Fluorous Solid Phase Extraction".
  3. FTI Application Note "Fluorous Thiols as Scavengers" 
  4. FTI Application Note "Fluorous Mixture Synthesis"
  5. Laura A. McAllister, Rosemary A. McCormick, Stephen Brand, and David J. Procter “A Fluorous-Phase Pummerer Cyclative-Capture Strategy for the Synthesis of Nitrogen Heterocycles” Angew. Chem. Int. Ed. 2005, 44, 452–455.
  6. Laura A. McAllister, Rosemary A. McCormick, Karen M. James, Stephen Brand, Nigel Willetts, David J. Procter “A Fluorous, Pummerer Cyclative-Capture Strategy for the Synthesis of N-Heterocycles” Chemistry - A European Journal 2007, 13, 1032-1046.
  7. David Horhant, Anne-Cécile Le Lamer, Joël Boustie, Philippe Uriac and Nicolas Gouault “Separation of a Mixture of Paraconic Acids from Cetraria islandica (L.) Ach. Employing a Fluorous Tag – Catch and Release Strategy” Tetrahedron Letters 2007, 48, 6031-6033.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C8F17 1H,1H,2H,2H-Perfluorodecane-1-thiol
34143-74-3
C10H5F17S
F017023-0002 2g Inquire
    FW:  480.15 F017023-0010 10g Inquire
      F017023-0025 25g Inquire
      F017023-0100 100g Inquire