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Protecting groups and

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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.

 
 
Silanes
 

 

F-silanes are the fluorous equivalent to a TIPS group and exhibit properties similar to most silicon protecting groups and have been used in both parallel and fluorous mixture synthesis.  Tagging of an alcohol is accomplished by in- situ activation of the F-silane to either the bromide of triflate followed by addition of the alcohol.  Detagging of the F-silane is accomplished either by treatment with fluoride or acid.  F017004, the C8F17 analog of F-silane has appropriate fluorine content for the tagging of diverse organic molecules and is recommended for natural product or medicinal chemistry synthesis in combination with fluorous solid phase extraction.  The other F-silane homologs are useful in fluorous HPLC and fluorous mixture synthesis.

 

  1. Luo, Z. Y., Zhang, Q., Oderaotoshi, Y., Curran, D. P. Science, 2001, 291, 1766.
  2. Zhang, W., Luo, Z., Chen, C.H., Curran, D.P.J. Am. Chem. Soc. 2002, 124, 10443.
  3. Curran, D. P.  Synlett 2001, 1488.
  4. Please refer to FTI Application Note "Fluorous Solid Phase Extraction"
  5. Emma R. Palmacci, Michael C. Hewitt, and Peter H. Seeberger “Cap-Tag–Novel Methods for the Rapid Purification of Oligosaccharides Prepared by Automated Solid-Phase Synthesis” Angew. Chem. Int. Ed. 2001, 40, 4433-4437.
  6. Leonardo Manzoni “Rapid synthesis of oligosaccharides using an anomeric fluorous silyl protecting group”Chem. Commun., 2003, 2930–2931.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C3F7 Diisopropyl-(1H,1H,2H,2H-perfluoropentyl)silane  
C11H19F7Si
F007004-0002 2g Inquire
    FW: 312.39   F007004-0010 10g Inquire
      F007004-0025 25g Inquire
      F007004-0100 100g Inquire
     
C4F9 Diisopropyl-(1H,1H,2H,2H-perfluorohexyl)silane
356056-13-8
C12H19F9Si
F009004-0002 2g Inquire
    FW:  262.40 F009004-0010 10g Inquire
      F009004-0025 25g Inquire
      F009004-0100 100g Inquire
     
C6F13 Diisopropyl-(1H,1H,2H,2H-perfluorooctyl)silane
356056-14-9
C14H19F13Si
F013004-0002 2g Inquire
    FW:  462.42 F013004-0010 10g Inquire
      F013004-0025 25g Inquire
      F013004-0100 100g Inquire
     
(CF2)4CF(CF3)2 Diisopropyl-(1H,1H,2H,2H-perfluoro-7-methyloctyl)silane  
C15H19F15Si
F015004-0002 2g Inquire
    FW:  512.43 F015004-0010 10g Inquire
      F015004-0025 25g Inquire
      F015004-0100 100g Inquire
     
C8F17 Diisopropyl-(1H,1H,2H,2H-perfluorodecyl)silane
356056-15-0
C16H19F17Si
F017004-0002 2g Inquire
    FW:  562.44 F017004-0010 10g Inquire
      F017004-0025 25g Inquire
      F017004-0100 100g Inquire
     
(CF2)6CF(CF3)2 Diisopropyl-(1H,1H,2H,2H-perfluoro-9-methyldecyl)silane  
C17H19F19Si
F019004-0002 2g Inquire
    FW:  612.45 F019004-0010 10g Inquire
      F019004-0025 25g Inquire
      F019004-0100 100g Inquire
     
C10F21 Diisopropyl-(1H,1H,2H,2H-perfluorododecyl)silane
356056-16-1
C18H19F21Si
F021004-0002 2g Inquire
    FW:  662.46 F021004-0010 10g Inquire
      F021004-0025 25g Inquire
      F021004-0100 100g Inquire