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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.

 
 
Benzyl alcohol

Fluorous benzyl alcohol is the fluorous equivalent of benzyl alcohol.  Tagging of carboxylic acids and alcohols is conducted analogously to that of traditional benzyl alcohol.  F017026, the C8F17 analog 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 homologs are useful in fluorous HPLC and fluorous mixture synthesis.

 

1. Curran, D. P.; Oderaotoshi, Y. Tetrahedron 2001, 57, 5243-5253.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C3F7 4-(1H,1H,2H,2H-Perfluoropentyl)benzyl alcohol  
C12H11F7O
F007026-0002 2g Inquire
    FW:  304.23 F007026-0010 10g Inquire
      F007026-0025 25g Inquire
      F007026-0100 100g Inquire
     
C4F9 4-(1H,1H,2H,2H-Perfluorohexyl)benzyl alcohol  
C13H11F9O
F009026-0002 2g Inquire
    FW:  354.24 F009026-0010 10g Inquire
      F009026-0025 25g Inquire
      F009026-0100 100g  
     
C6F13 4-(1H,1H,2H,2H-Perfluorooctyl)benzyl alcohol
356055-76-0
C15H11F13O
F013026-0002 2g Inquire
    FW:  454.26 F013026-0010 10g Inquire
      F013026-0025 25g Inquire
      F013026-0100 100g  
     
(CF2)4CF(CF3)2 4-(1H,1H,2H,2H-Perfluoro-7-methyloctyl)benzyl alcohol  
C16H11F15O
F015026-0002 2g Inquire
    FW:  504.27 F015026-0010 10g Inquire
      F015026-0025 25g Inquire
      F015026-0100 100g Inquire
     
C8F17 4-(1H,1H,2H,2H-Perfluorodecyl)benzyl alcohol
356055-77-1
C17H11F17O
F017026-0002 2g Inquire
    FW:  554.28 F017026-0010 10g Inquire
      F017026-0025 25g Inquire
      F017026-0100 100g  
     
(CF2)6CF(CF3)2 4-(1H,1H,2H,2H-Perfluoro-9-methyldecyl)benzyl alcohol  
C18H11F19O
F019026-0002 2g Inquire
    FW:  604.29 F019026-0010 10g Inquire
      F019026-0025 25g Inquire
      F019026-0100 100g Inquire
     
C10F21 4-(1H,1H,2H,2H-Perfluorododecyl)benzyl alcohol  
C19H11F21O
F021026 Please Inquire for Pricing & Availability
    FW:  654.3