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If your email does not support graphics, click here to
view a web page. Our product catalog has been updated with innovative fluorous
protecting groups and scavengers. Click here to download the
latest pdf version. Please note that some catalog numbers have changed.
Fluorous Technologies,
Inc.
Fluorous Technologies, Inc. (FTI) is a chemical
technology company dedicated to the development and commercialization of fluorous
products focused at the life science market. The company employs patented
technology to solve unmet synthesis and separation problems across the entire
drug development process. FTI further leverages its enabling technology through
service contracts, licenses, and collaborations.
Solution Phase Scavengers Take
Hold
A June 2002 article in Modern Drug Discovery Magazine entitled
"Combichem
Scavenging" highlights why solid phase synthesis and scavenger resins have
come into favor. The article reports that "synthesis in solution makes up only
30% of libraries produced the most important [reason for this] is the difficulty
of removing leftovers from previous reactions or unwanted byproducts that might
interfere with subsequent chemistry." Fluorous technology is being used by
medicinal and combinatorial chemists worldwide to tackle this daunting separation
issue. Fluorous-tagged scavengers are the solution-phase alternative to
solid-bound scavengers. Fluorous
solution phase scavengers capture excess reagents and a simple solid phase
extraction over FluoroFlash (TM) silica gel removes both the scavenged
products and any excess scavenger. Compared to related solid phase scavenging
reactions, the fluorous reactions are faster, cleaner, and do not require large
excesses of scavenging reagents. Innovative fluorous scavenging methods
are introduced in a recent publication in Tetrahedron Letters by medicinal
chemists Lindsley, Zhao, and Leister of Merck Research Laboratories
entitled "Fluorous-Tethered
Quenching Reagents for Solution Phase Parallel Synthesis" To fuel this
area of research, FTI has recently expanded its product offering to include the
following Nucleophilic (F-Thiol, F-Propylamine, and F-Benzylamine) and
Electrophilic (F-Ethyl Isocyanate, F-Oxybenzaldehyde, and F-Isatoic Anhydride)
scavengers. In recent published work entitled "Use
of fluorous silica gel to separate thiol quenching derivatives
in solution-phase parallel synthesis,"[2]
researchers at FTI used commercially available fluorous thiols (RfCH2CH2SH)
combined with FluoroFlash™silica
gel SPE to remove excess electrophiles in the parallel
synthesis of a tertiary amine library. Fluorous quenching
conducted in a homogenous medium had favorable reaction kinetics
and in a side by side comparison required less amount of
scavenging reagent as compared to solid-bound scavengers.
In addition, the quenching reaction using a fluorous thiol
was found to be 5-10 times faster than that
of a polymer-supported thiol. To learn more about this application,
contact Dr. Wei Zhang.
Enantiomer Synthesis
– Racemic, Asymmetric, or Fluorous Quasiracemic?
Like asymmetric synthesis, fluorous quasiracemic synthesis
starts and finishes with enantiopure compounds, but like racemic
synthesis, it provides both enantiomers in a single synthesis.
In a paper entitled "Quasiracemic
Synthesis: Concept and Implementation with a Fluorous Tagging
Strategy to make Both Enantiomers of Pyridovericin and Mappicine,"
Curran and coworkers showed that by tagging two enantiomeric
starting materials, a "quasiracemic" mixture could be made.
After several synthetic steps, the mixture was separated by
FluoroFlash™ HPLC to deliver both product enantiomers.
This is the simplest application of a powerful technique
called fluorous
mixture synthesis (FMS) in which up to 7 substrates may
be tagged, mixed, reacted as a single mixture through several
synthetic steps, and separated by fluorous HPLC. The result
is pure compounds, predictably eluted and identified based
on fluorous tag length. A detailed application of FMS can
be found in a Journal of the American Chemical Society article
entitled, "Solution-Phase
Preparation of a 560-Compound Library of Individual Pure Mappicine
Analogues by Fluorous Mixture Synthesis."
Fluorous
Catalysts Ease Product Separation
Homogeneous catalysts are useful tools in organic synthesis,
but often removal of such catalysts from the desired products
requires time-consuming purification steps. For high-throughput
synthesis, quick and reliable methods to isolate the product
are critical. Pozzi and coworkers recently employed a lightly
fluorinated chiral cobalt-salen complex for hydrolytic
kinetic resolution of racemic terminal epoxides.
The fluorous-tagged catalyst used was readily soluble in common
organic solvents and the reactivity and enantioselectivity
in the reactions investigated were comparable to those obtained
with non-fluorinated catalysts.
Pozzi and coworkers reported that the use of a lightly fluorinated
catalyst in combination with fluorous SPE (loading of the
reaction mixture onto fluorous silica gel and elution with
a ‘fluorophobic’ solvent) facilitated the isolation of desired
products: "Solid-liquid extraction was found to be the quickest
and operationally simplest way to get rid of the catalyst:
it did not require the use of a fluorous solvent and could
be useful in parallel synthesis." Combining a lightly fluorinated
catalyst with FluoroFlash™ SPE delivers a practical
solution to simplify the isolation step in homogeneous catalytic
reactions and deliver ‘catalyst-free’ products.
Seeking Scientists
Ready to work in an exciting and challenging new area of chemistry
for an emerging leader in the chemical technology industry?
If so, FTI is currently seeking Bachelor, Master's and Ph.D.
scientists with experience in synthetic organic chemistry,
medicinal chemistry, library generation, process R&D, or process
chemistry. Click here
to submit your resume today!
For further information please contact Dr.
Philip E. Yeske at 412-826-3051. We value your privacy.
To learn more about how FTI uses personal information, click
here. To unsubscribe
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