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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.

 
 
PMB OH
 

 

F-PMB-OH is the fluorous equivalent of p-methoxybenzyl alcohol (PMB-OH) used in protecting alcohols in multi-step organic synthesis.  F-PMB is deprotected either under acid or oxidizing conditions.  The reactivity of F-PMB and conventional PMB are so similar that a DMB protecting group has been selectively cleaved in the presence of both F-PMB and PMB (1).  F017006, 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 (2).

 

  1. Curran, D.P., Furukawa, T.  Organic Letters, 2002, 2233.
  2. Curran, D.P.  Synlett 2001, 1488.
  3.  Please refer to FTI Application Note "Fluorous Solid Phase Extraction"
  4. Xiao Wang, Scott G. Nelson and Dennis P. Curran “The azido acid approach to β-peptides: parallel synthesis of a tri-β-peptide library by fluorous tagging” Tetrahedron 2007, 63, 6141-6145.
  5. Pierre-Yves Dakas, Sofia Barluenga, Frank Totzke, Ute Zirrgiebel, Nicolas Winssinger “Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase InhibitorsAngewandte Chemie International Edition 2007, 46, 6899-6902.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C3F7 4-[3-(Perfluoropropyl)propyl-1-oxy]benzyl alcohol  
C13H13F7O2
F007006 Please Inquire for Pricing & Availability
    FW:  334.26      
     
C4F9 4-[3-(Perfluorobutyl)propyl-1-oxy]benzyl alcohol  
C14H13F9O2
F009006-0002 2g Inquire
    FW:  384.27 F009006-0010 10g Inquire
      F009006-0025 25g Inquire
     
C6F13 4-[3-(Perfluorohexyl)propyl-1-oxy]benzyl alcohol  
C16H11F13O2
F013006-0002 2g Inquire
    FW:  484.29 F013006-0010 10g Inquire
      F013006-0025 25g Inquire
     
C7F15 4-[3-(Perfluoroheptyl)propyl-1-oxy]benzyl alcohol  
C17H13F15O2
F015006 Please Inquire for Pricing & Availability
    FW:  534.30      
     
C8F17 4-[3-(Perfluorooctyl)propyl-1-oxy]benzyl alcohol  
C18H13F17O2
F017006-0002 2g Inquire
    FW:  584.31 F017006-0010 10g Inquire
      F017006-0025 25g Inquire
      F017006-0100 100g Inquire