Rf-tagged Protecting Groups—Temporary, Cleavable, Fluorous Tags

Chemfiles Volume 4 Article 9

F-Boc-ON

F-Boc-ON is the fluorous equivalent of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile (Boc-ON) used in protecting amino groups in peptide synthesis or other functionalities in multi-step organic synthesis. Protection of the amino group with F-Boc-ON and deprotection are achieved under traditional reaction conditions, with the advantage that products containing the F-Boc group can easily be separated from organic reagents, reactants, or products by performing a quick fluorous solid-phase extraction over FluoroFlash® Silica Gel (see sections 8 and 9).[1,2]

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F-Cbz-OSu

F-Cbz-OSu is the fluorous equivalent of benzyloxycarbonyloxysuccin-imide (Cbz-OSu) used in protecting amino groups in peptide synthesis or multi-step organic synthesis. Protection of the amino group with F-Cbz-OSu and subsequent deprotection are achieved with traditional reaction conditions, with the advantage that products containing the F-Cbz group can easily be separated from organic reagents, reactants, or products by performing a quick fluorous solid-phase extraction over FluoroFlash® Silica Gel (see sections 8 and 9).[3,4]

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F-PMB-OH

F-PMB-OH is the fluorous equivalent of p-methoxybenzyl alcohol (PMB-OH) used in protecting alcohols in multi-step organic synthesis.

Protection of an alcohol with F-PMB-OH and deprotection are achieved under traditional reaction conditions.[5,6]

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FluoMar™

FluoMar is the fluorous equivalent of the Marshall resin used frequently as a carbonate and carbamate linker in solid-phase syntheses.[7,8] This reagent can be used as an alternative to the Marshall resin in solution-phase combinatorial and parallel synthesis. Tagging of substrates is achieved with traditional reaction conditions, with the advantage that products or intermediates containing the tag (FluoMar) group can easily be separated from organic reagents, reactants or products by performing a quick solid-phase extraction over FluoroFlash® silica gel.[9]

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Materials

     

References

  1. Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D. P. J. Org. Chem. 2001, 66, 4261.
  2. Curran, D. P. Synlett 2001, 1488.
  3. Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. J.Org. Chem. 2003, 68, 4643
  4. Curran, D. P. Synlett 2001, 1488.
  5. Curran, D. P.; Furukawa, T. Org. Lett. 2002, 2233
  6. Curran, D. P. Synlett 2001, 1488.
  7. Chen, C. H.-T.; Zhang, W. Org. Lett. 2003, 5, 1015
  8. Marshall, D. L.; Liener, I. E. J. Org. Chem. 1970, 35, 867
  9. Curran, D. P. Synlett 2001, 1488.

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