Fluorous 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.

Boc-ON

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

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

Silanes

FTI Products: F009004 (18976), F013004 (00454), F017004 (04537)

F-silanes are the fluorous equivalent to a TIPS group and exhibit properties similar to most silicon protecting groups and have been used in both parallel and fluorous mixture synthesis. Tagging of an alcohol is accomplished by in- situ activation of the F-silane to either the bromide of triflate followed by addition of the alcohol. Detagging of the F-silane is accomplished either by treatment with fluoride or acid.
Application Note

Cbz-OSu

FTI Products: F009008 (00246), F013008 (05656), F017008 (14944)

F-Cbz-OSu is the fluorous equivalent of benzyloxycarbonyl oxysuccinimide (Cbz-OSu) used primarily in the protection of amino groups in peptide synthesis or multi-step organic synthesis. Deprotection of the F-Cbz group is achieved under the same conditions as traditional Cbz such as hydrogenation or hydride reduction.
Application Note

PMB-OH

FTI Products: F009006 (01452), F013006 (67772), F017006 (97071)

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.
Application Note

Benzyl Alcohol

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

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® 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)

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 Chloride (DMT-Cl)

FTI Products: F017063 (672580)

Monomethoxy Trityl Chloride (MMT-Cl)

FTI Products: F017235 (672149)

Fmoc-Cl

FTI Products: F026229 (672262)

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