Fluorous Mixture Synthesis

Benefits of Fluorous Mixture Synthesis (FMS)

  • Leverage your synthetic effort
  • Multiply the compounds obtained per reaction step
  • Easily re-synthesize single compounds using exact same chemistry
  • Design predictable and reliable fluorous HPLC separations into your workflow

Fluorous Mixture Synthesis Explained

Predictable separation of diverse mixtures of fluorous tagged compounds can be accomplished based on the length and number of fluorous tags by FluoroFlash® HPLC. Fluorous Mixture Synthesis (FMS) takes advantage of this unique property of fluorous compounds to allow multiple reactions to be conducted in a single well or flask. A series of substrates are tagged with a corresponding series of homologous FluoroFlash® tags. During separation, the molecules elute in order of increasing fluorine content of the tag. Compounds are predictably identifiable by simple comparison to the original tag/substrate pairings (figure 2). The tags are then removed via chemical transformation followed by fluorous SPE to yield the pure target products.

Fluorous Mixture Synthesis dramatically reduces the number of individual reactions and separations that need to be run in library production, thereby increasing productivity. Unlike solid phase mix-and-split procedures, the solution phase nature of FMS allows for easy adoption of existing literature methods reducing reaction development time. Reactions can be monitored using standard analytical methods ensuring optimal conversion with minimal use of reagents. The inertness of the fluorous tags results in an increased diversity of reactions and scaffolds that can be accessed versus other methods, since the fluorous tag does not limit the chemistry that can be conducted. Finally, any compounds of interest identified can be easily resynthesized using the same exact chemistry as the library.

Fluorous Mixture Synthesis and Natural Product Synthesis

The Curran Group skillfully employs fluorous mixture synthesis to leverage their natural product synthesis. The value of FMS is evident in their work. Long synthetic sequences (> 30 steps) are often necessary to get to the target compound. By using fluorous mixture synthesis, the Curran Group is able to make many varities of their target with the same effort that it would take to make a single compound. The multiple isomers that they obtain are then compared to the naturally isolated compound, making it easier to confirm the structure. Without fluorous mixture synthesis, synthesis (or re-synthesis) of these stereoisomers would take a great deal of time and resources.

Start Making Your Own Mixtures

Fluorous Technologies Inc. can provide you with everything you need to conduct fluorous mixture synthesis. We offer tags in various fluorous lengths, fluorous SPE cartridges, fluorous HPLC columns, and expertise in planning and executing your synthesis. For further reading about fluorous mixture synthesis, please review the links under the Related Products and For More Information sections to your left.

Selected References

  • Zhang, W.; Luo, Z.; Chen, C. H.-T.; Curran, D. P. Journal of the American Chemical Society 2002, 124, 10443-10450.
  • Jung, W.-H.; Guyenne, S.; Riesco-Fagundo, C.; Mancuso, J.; Nakamura, S.; Curran, D. P. Angew. Chem., Int. Ed. Angewandte Chemie, International Edition, 2008, 47, 1130-1133.
  • Curran, D.P.; Furukawa, T. Simultaneous Preparation of Four Truncated Analogues of Discodermolide by Fluorous Mixture Synthesis, Organic Letters, 2002, 2233-2235.