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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.

 
 
Boc-ON
 

 

F-Boc-ON is the fluorous equivalent of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) primarily used in the protection of amines.  Analogous to conventional Boc, the fluorous Boc group is acid labile, but stable to a wide range of basic and nucleophilic conditions.  F017003, the C8F17 analog of F-Boc 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-Boc homologs are useful in fluorous HPLC and fluorous mixture synthesis.

  1. Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D.P. J.Org Chem. 2001, 66, 4261.
  2. 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, pp 222-236.
  3. Curran, D. P.  Synlett 2001, 1488.  Curran, D. P. ‘Separations with Fluorous Silica Gel and Related Materials’, in Handbook of Fluorous Chemistry; Wiley-VCH: Weinheim, 2004; pp 101-127.
  4. FTI Application Note "Fluorous Solid Phase Extraction"
  5. Zhang, W. Arkivoc 2004 (i), 101-109.
  6. Zhang, W. Tempest, P. “Highly Efficient Microwave-Assisted Fluorous Ugi and Post-Condensation Reactions for Benzimidazoles and Quinoxalinones” Tetrahedron Lett. 2004, 45, 6757-6760.
  7. 7) Sreeman K. Mamidyala and Steven M. Firestine “Fluorous synthesis of minor groove binding agents related to distamycin” Tetrahedron Lett. 2006, 47, 7431-7434.

 

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C3F7 2-[2-(1H,1H,2H,2H-Perfluoropentyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C17H15F7N2O3
F007003-0002 2g Inquire
    FW:  428.34 F007003-0010 10g Inquire
      F007003-0025 25g Inquire
      F007003-0100 100g Inquire
     
C4F9 2-[2-(1H,1H,2H,2H-Perfluorohexyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C18H15F9N2O3
F009003-0002 2g Inquire
    FW:  478.35 F009003-0010 10g Inquire
      F009003-0025 25g Inquire
      F009003-0100 100g Inquire
     
C6F13 2-[2-(1H,1H,2H,2H-Perfluorooctyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C20H15F13N2O3
F013003-0002 2g Inquire
    FW:  578.37 F013003-0010 10g Inquire
      F013003-0025 25g Inquire
      F013003-0100 100g Inquire
     
(CF2)4CF(CF3)2 2-[2-(1H,1H,2H,2H-Perfluoro-7-methyloctyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C21H15F15N2O3
F015003-0002 2g Inquire
    FW:  628.38 F015003-0010 10g Inquire
      F015003-0025 25g Inquire
      F015003-0100 100g Inquire
     
C8F17 2-[2(1H,1H,2H,2H-Perfluorodecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile
3350716-42-6
C22H15F17N2O3
F017003-0002 2g Inquire
    FW:  678.39 F017003-0010 10g Inquire
      F017003-0025 25g Inquire
      F017003-0100 100g Inquire
     
(CF2)6CF(CF3)2 2-[2-(1H,1H,2H,2H-Perfluoro-9-methyldecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C23H15F19N2O3
F019003-0002 2g Inquire
    FW:  728.40 F019003-0010 10g Inquire
      F019003-0025 25g Inquire
      F019003-0100 100g Inquire
     
C10F21 2-[2-(1H,1H,2H,2H-Perfluorododecyl) isopropoxycarbonyloxyimino]-2-phenylacetonitrile  
C24H15F21N2O3
F021003-0002 2g Inquire
    FW:  778.41 F021003-0010 10g Inquire
      F021003-0025 25g Inquire
      F021003-0100 100g Inquire