♦ Boc-ON
♦ Silanes
♦ PMB OH
♦ t-Butanol
♦ Cbz-Osu
♦ Thiol
♦ Benzyl alcohol
♦ FluoMar
♦ Oxybenzaldehyde
♦ Fmoc
♦ Trityl Chlorides
♦ Trityl Alcohols
♦ Thiophenol |
Fluorous tags are perfluoroalkyl modified versions of traditional protecting groups familiar to synthetic organic chemists. Conceptually they are very similar to solid phase tags, but fluorous tags and fluorous tagged substrates are soluble in most organic solvents, such as DMF, THF, CH2Cl2, etc. This provides some distinct advantages over solid phase tagging strategies including solution phase kinetics, complete control of reaction stoichiometry, and the ability to monitor reactions easily using traditional analytical techniques, including TLC, NMR, GC, LC/MS, and IR. The fluorous tagged materials are easily separated from non-tagged components by F-SPE. Fluorous tags have been used in a variety of total, parallel, and mixture syntheses (1-3).
1. Zhang, W. “Fluorous Protecting Groups and Tags” in Handbook of Fluorous Chemistry Gladysz, J. A.; Curran, D. P.; Horvath, I. T. Eds. Wiley-VCH, 2004, pp222-2362.
2. Zhang, W. “Fluorous Tagging Strategy for Solution-Phase Synthesis of Small Molecules, Peptides and Oligosaccharides” Curr. Opin. Drug Disov. Develop. 2004, 7, 784-797.
3. Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000, p 25-37.
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PMB OH
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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. The reactivity of F-PMB and conventional PMB are so similar that a DMB protecting group has been selectively cleaved in the presence of both F-PMB and PMB (1). F017006, the C8F17 analog has appropriate fluorine content for the tagging of diverse organic molecules and is 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 (2).
- Curran, D.P., Furukawa, T. Organic Letters, 2002, 2233.
- Curran, D.P. Synlett 2001, 1488.
- Please refer to FTI Application Note "Fluorous Solid Phase Extraction"
- Xiao Wang, Scott G. Nelson and Dennis P. Curran “The azido acid approach to β-peptides: parallel synthesis of a tri-β-peptide library by fluorous tagging” Tetrahedron 2007, 63, 6141-6145.
- Pierre-Yves Dakas, Sofia Barluenga, Frank Totzke, Ute Zirrgiebel, Nicolas Winssinger “Modular Synthesis of Radicicol A and Related Resorcylic Acid Lactones, Potent Kinase Inhibitors” Angewandte Chemie International Edition 2007, 46, 6899-6902.
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