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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.

 
 
Fmoc

 

F-Fmoc-Osu is the fluorous equivalent of conventional Fmoc.  F-Fmoc is base labile and is detagged under similar conditions. F026005, the bis-C6F13 analog of Fmoc, has appropriate fluorine content for the tagging of diverse organic molecules and is recommended for N-terminal fluorous tagging with F-SPE purification. 

Rf NAME/CAS# PROPERTIES CATALOG# QTY PRICE
C6F13

N-[2,7-Bis(1H,1H,2H,2H-perfluorooctyl)-9-fluorenylmethoxycarbonyloxy]succinimide

C35H21F26NO5 F026005-0001 1g Inquire
 
FW:  1029.52
F026005-0002 2g Inquire
      F026005-0010 10g Inquire
      F026005-0025 25g Inquire
           
           
Fmoc-Chloroformate
  Fmoc chloroformate
C6F13

2,7-Bis(1H,1H,2H,2H-perfluorooctyl)-9-fluorenylmethoxycarbonyl chloride  

C31H17ClF26O2 F026229-0001 1g Inquire
    FW:  950.90 F026229-0002 2g Inquire
      F026229-0010 10g Inquire
      F026229-0025 25g Inquire