Home
 
 
Protecting groups and tags

Click on links below to change displayed product

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.

 

 
 
FluoMar®
 

 

FluoMar® is the solution phase equivalent of Marshall resin used in combinatorial and parallel synthesis.  FluoMar® has been used a stable acid activator for the formation of amides (1).  F017027, the C8F17 analog of FluoMar® 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 FluoMar® homologs are useful in fluorous HPLC and fluorous mixture synthesis.

 

1. Chen, C. H.-T.; Zhang, W. Org. Lett. 2003, 5, 1015-1017.

 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C3F7 4-(1H,1H,2H,2H-Perfluoropentyl-1-thio)-phenol  
C11H9F7OS
F007027 Please Inquire for Pricing & Availability
    FW:  322.20      
     
C4F9 4-(1H,1H,2H,2H-Perfluorohexyl-1-thio)-phenol  
C12H9F9OS
F009027-0010 10g Inquire
    FW:  372.21 F009027-0025 25g Inquire
      F009027-0100 100g Inquire
     
C6F13 4-(1H,1H,2H,2H-Perfluorooctyl-1-thio)-phenol  
C14H9F13OS
F013027-0010 10g Inquire
    FW:  472.23 F013027-0025 25g Inquire
      F013027-0100 100g Inquire
     
(CF2)4CF(CF3)2 4-(1H,1H,2H,2H-perfluoro-7-methyloctyl-1-thio)-phenol  
C15H9F15OS
F015027-0010 10g Inquire
    FW:  522.24 F015027-0025 25g Inquire
      F015027-0100 100g Inquire
     
C8F17 4-(1H,1H,2H,2H-Perfluorodecyl-1-thio)-phenol
142623-70-9
C16H9F17OS
F017027-0010 10g Inquire
    FW:  572.25 F017027-0025 25g Inquire
      F017027-0100 100g Inquire
     
(CF2)6CF(CF3)2 4-(1H,1H,2H,2H-perfluoro-9-methyldecyl-1-thio)-phenol  
C17H9F19OS
F019027-0010 10g Inquire
    FW:  622.26 F019027-0025 25g Inquire
      F019027-0100 100g Inquire
     
C10F21 4-(1H,1H,2H,2H-Perfluorododecyl-1-thio)-phenol  
C18H9F21OS
F021027 Please Inquire for Pricing & Availability
    FW:  672.27