Fluorous Chemistry

Protecting Groups and Tags


FluoroFlash® tags are perfluoroalkyl modified versions of traditional protecting groups familiar to synthetic chemists. These tags have reactivity profiles very similar to the traditional protecting group, but provide the added benefit of providing a phase tag for purification. FluoroFlash® tags are a solution phase alternative to solid phase synthesis strategies. The fluorous-tagged materials are easily separated from non-tagged components by F-SPE. The C8F17 analogs have appropriate fluorine content for the tagging of diverse organic molecules and are 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 applications.

Fluorous Protecting Groups and Tags Structure Image
Benefits of FluoroFlash® Tags:
  • Solution phase kinetics

  • Broad reaction compatibility

  • Reaction monitoring by TLC, GC, LC, NMR, etc.

  • Readily scalable

Boc-ON


 

FTI Products: F009003 (01382), F013003 (11807), F017003 (55118)

Boc-ON Structure Image

F-Boc-ON is the fluorous equivalent of 2-(t-butoxycarbonyloxyimino)-2-phenylacetonitrile (BOC-ON) primarily used in the protection of amines. Analogous to conventional Boc, the fluorous Boc group is acid labile, but stable to a wide range of basic and nucleophilic conditions.
Application Note



Benzyl Alcohol


 

FTI Products: F009026 (08431), F013026 (16638), F017026 (19563)

Benzyl Alcohol Structure Image

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.



FluoMar®


 

FTI Products: F009027 (43849), F013027 (43893), F017027 (40829)

FluoMar Structure Image

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.
Application Note



Trityl Alcohol


 

FTI Products: F017062 (672475)

FluoMar Structure Image

F-Trt is the fluorous analog to traditional Trt and is used in the protection of amino acid side chains including Asn, Asp, Gln, Glu, His, Ser, Thr, Tyr.



Dimethoxy Trityl Alcohol (DMT-OH)


 

FTI Products: F017064 (672696)

Dimethoxy Trityl Alcohol (DMT-OH) Structure Image



Dimethoxy Trityl Chloride (DMT-Cl)


 

FTI Products: F017063 (672580)

Dimethoxy Trityl Chloride (DMT-Cl) Structure Image



Monomethoxy Trityl Chloride (MMT-Cl)


 

FTI Products: F017235 (672149)

Monomethoxy Trityl Chloride (MMT-Cl) Structure Image



Fmoc-Cl


 

FTI Products: F026229 (672262)

Fmoc-Cl Structure Image

Base labile protecting group/tag for nitrogens; fully compatible with conventional Fmoc chemistries.