Fluorous tagging strategy for solution-phase synthesis of small molecules, peptides and oligosaccharides.
The purification of reaction mixtures is a slow process in organic synthesis, especially during the production of large numbers of analogs and compound libraries. Phase-tag methods such as solid-phase synthesis and fluorous synthesis, provide efficient ways of addressing the separation issue. Fluorous synthesis employs functionalized perfluoroalkyl groups attached to substrates or reagents. The separation of the resulting fluorous molecules can be achieved using strong and selective fluorous liquid-liquid extraction, fluorous silica gel-based solid-phase extraction or high-performance liquid chromatography. Fluorous technology is a novel solution-phase method, which has the advantages of fast reaction times in homogeneous environments, being readily adaptable to literature conditions, having easy intermediate analysis, and having flexibility in reaction scale and scope. In principle, any synthetic methods that use a solid-support could be conducted in solution-phase by replacing the polymer linker with a corresponding fluorous tag. This review summarizes the progress of fluorous tags in solution-phase synthesis of small molecules, peptides and oligosaccharides.
Zhang
Wei
W
Fluorous Technologies Inc, University of Pittsburgh Applied Research Center, Pittsburgh, PA 15238, USA. w.zhang@fluorous.com
D005459:Fluorides / Q000737:chemistry*; D007202:Indicators and Reagents; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*
D007202:Indicators and Reagents; D009844:Oligosaccharides; D010455:Peptides; D005459:Fluorides