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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.

 
 
F-Cbz-Osu
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F-Cbz-OSu is the fluorous equivalent of benzyloxycarbonyl oxysuccinimide (Cbz-OSu) used primarily in the protection of amino groups in peptide synthesis or multi-step organic synthesis.  Deprotection of the F-Cbz group is achieved under the same conditions as traditional Cbz such as hydrogenation or hydride reduction.  F017008, the C8F17 analog of F-Cbz 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-Cbz homologs are useful in fluorous HPLC and fluorous mixture synthesis.

 

  1. Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z J.Org.Chem. 2003, 68, 4643.
  2. Curran, D. P.  Synlett  2001, 1488.
  3. Please refer to FTI Application Note "Fluorous Solid Phase Extraction"
  4. Dmitri V. Filippov, Dirk J. van Zoelen, Steven P. Oldfield, Gijs A. van der Marel, Herman S. Overkleeft, Jan W. Drijfhout and Jacques H. van Boom “Use of benzyloxycarbonyl (Z)-based fluorophilic tagging reagents in the purification of synthetic peptides” Tetrahedron Lett. 2002, 43, 7809–7812.
  5. Dominik Schwinn, Willi Bannwarth “Perfluoro-Tagged Benzyloxycarbonyl Protecting Group and Its Application in Fluorous Biphasic Systems” Helv. Chim. Acta 2002, 85, 255-264.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY
C3F7 N-[4-(1H,1H,2H,2H-Perfluoropentyl)benzyloxycarbonyloxy]succinimide  
C17H14F7NO5
F007008-0002 2g
    FW:  445.32 F007008-0010 10g
      F007008-0025 25g
      F007008-0100 100g
     
C4F9 N-[4-(1H,1H,2H,2H-Perfluorohexyl)benzyloxycarbonyloxy]succinimide  
C18H14F9NO5
F009008-0002 2g
    FW:  495.33 F009008-0010 10g
      F009008-0025 25g
     
C6F13 N-[4-(1H,1H,2H,2H-Perfluorooctyl)benzyloxycarbonyloxy]succinimide  
C20H14F13NO5
F013008-0002 2g
    FW:  595.32 F013008-0010 10g
      F013008-0025 25g
     
(CF2)4CF(CF3)2 N-[4-(1H,1H,2H,2H-Perfluoro-7-methyloctyl)benzyloxycarbonyloxy]succinimide  
C21H14F15NO5
F015008-0002 2g
    FW:  645.36 F015008-0010 10g
      F015008-0025 25g
      F015008-0100 100g
     
C8F17 N-[4-(1H,1H,2H,2H-Perfluorodecyl)benzyloxycarbonyloxy]succinimide
356056-15-0
C22H14F17NO5
F017008-0002 2g
    FW:  695.34 F017008-0010 10g
      F017008-0025 25g
     
(CF2)6CF(CF3)2 N-[4-(1H,1H,2H,2H-Perfluoro-9-methyldecyl)benzyloxycarbonyloxy]succinimide  
C23H14F19NO5
F019008-0002 2g
    FW:  745.38 F019008-0010 10g
      F019008-0025 25g
      F019008-0100 100g
     
C10F21 N-[4-(1H,1H,2H,2H-Perfluorododecyl)benzyloxycarbonyloxy]succinimide  
C24H14F21NO5
F021008
    FW:  795.39  
 

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