Polystyrene Wang NPC

Product information

Amines can be attached to the p-nitrophenyl carbonate resin to form the corresponding resin bound carbamates.
As an example the following compounds were synthesized by modifications on the resin bound carbamates: unsymetrical diamines, allylamines, guanidines, hydantoins, piperazines, triazolidienones, quinazoline diones ect.


L 54 Nitrophenyl Carbonate Resins

  1. Dixit, D. M.; Leznoff, C. C. Insoluble Polymer Supports as Monoblocking Agents of Symmetrical Diamines. J. Chem. Soc. Chem. Commun. 1977, No. 22, 798-799. doi: 10.1039/c39770000798.
  2. Dixit, D. M.; Leznoff, C. C. The Use of Polymer Supports in Organic Synthesis. 17. The Synthesis of Unsymmetrical Diamides and Monoamide Monotosylamides from Symmetrical Diamines. Isr. J. Chem. 1978, 17 (4), 248-252. doi: 10.1002/ijch.197800044.
  3. Giralt, E.; Rizo, J.; Pedroso, E. Application of Gel-Phase 13c-Nmr to Monitor Solid Phase Peptide Synthesis. Tetrahedron 1984, 40 (20), 4141-4152. doi: 10.1016/0040-4020(84)85095-4.
  4. Dressman, B. A.; Singh, U.; Kaldor, S. W. Solid Phase Synthesis of Urea Libraries Using a Diversifiable Thiophenoxy Carbonyl Linker. Tetrahedron Lett. 1998, 39 (22), 3631-3634. doi: 10.1016/s0040-4039(98)00652-2.
  5. Brady, S. F.; Stauffer, K. J.; Lumma, W. C.; Smith, G. M.; Ramjit, H. G.; Lewis, S. D.; Lucas, B. J.; Gardell, S. J.; Lyle, E. A.; Appleby, S. D.; Cook, J. J.; Holahan, M. A.; Stranieri, M. T.; Lynch, J. J., Jr; Lin, J. H.; Chen, I. W.; Vastag, K.; Naylor-Olsen, A. M.; Vacca, J. P. Discovery and Development of the Novel Potent Orally Active Thrombin Inhibitor N-(9-Hydroxy-9-Fluorenecarboxy)Prolyl Trans-4-Aminocyclohexylmethyl Amide (L-372,460): Coapplication of Structure-Based Design and Rapid Multiple Analogue Synthesis on Solid Support. J. Med. Chem. 1998, 41 (3), 401-406. doi: 10.1021/jm9705014.
  6. Yang, L. Facile Cleavage of the Carbamate Linker of Hydroxymethyl Resin and Its Application in Syntheses Requiring Strongly Acidic Conditions. Tetrahedron Lett. 2000, 41 (36), 6981-6984. doi: 10.1016/s0040-4039(00)01192-8.
  7. Ho, C. Y.; Kukla, M. J. Carbamate Linkers as Latent N-Methylamines in Solid Phase Synthesis. Tetrahedron Lett. 1997, 38 (16), 2799-2802. doi: 10.1016/s0040-4039(97)00510-8.
  8. Hauske, J. R.; Dorff, P. A Solid Phase CBZ Chloride Equivalent — a New Matrix Specific Linker. Tetrahedron Lett. 1995, 36 (10), 1589-1592. doi: 10.1016/0040-4039(95)00095-t.
  9. Li, W.-R.; Lin, Y.-S.; Yo, Y.-C. Lewis Acid-Catalyzed Cleavage of Carbamate and Carbonate Resins. Tetrahedron Lett. 2000, 41 (34), 6619-6622. doi: 10.1016/s0040-4039(00)01131-x.
  10. His, S.; Meyer, C.; Cossy, J.; Emeric, G.; Greiner, A. Solid Phase Synthesis of Amides by the Beckmann Rearrangement of Ketoxime Carbonates. Tetrahedron Lett. 2003, 44 (47), 8581-8584. doi: 10.1016/j.tetlet.2003.09.113.
  11. Park, K.-H.; Cox, L. J. Solid-Phase Synthesis of 1,2,4-Triazolidine-3,5-Diones. Tetrahedron Lett. 2002, 43 (21), 3899-3901. doi: 10.1016/s0040-4039(02)00701-3.
  12. Paio, A.; Gehanne, S.; Grandini, E.; Reginato, G.; Seneci, P. A New Analytical Method for Anchoring Quantification of Amines on Resin Support. Tetrahedron Lett. 2003, 44 (9), 1867-1870. doi: 10.1016/s0040-4039(03)00090-x.
  13. Salvino, J. M.; Gerard, B.; Ye, H. F.; Sauvagnat, B.; Dolle, R. E. The Solid-Phase Synthesis and Use of N-Monosubstituted Piperazines in Chemical Library Synthesis. J. Comb. Chem. 2003, 5 (3), 260-266. doi: 10.1021/cc020060w.
  14. Wang, C.-C.; Li, W.-R. Traceless Solid-Phase Synthesis of Substituted Benzimidazolones. J. Comb. Chem. 2004, 6 (6), 899-902. doi: 10.1021/cc049926j.
  15. Ghosh, A. K.; Hol, W. G. J.; Fan, E. Solid-Phase Synthesis of N-Acyl-N‘-Alkyl/Aryl Disubstituted Guanidines. J. Org. Chem. 2001, 66 (6), 2161-2164. doi: 10.1021/jo001420+.
  16. Crimmins, M. T.; Zuercher, W. J. Solid-Phase Synthesis of Carbocyclic Nucleosides. Org. Lett. 2000, 2 (8), 1065-1067. doi: 10.1021/ol005614n.
  17. Smith, A. L.; Stevenson, G. I.; Lewis, S.; Patel, S.; Castro, J. L. Solid-Phase Synthesis of 2,3-Disubstituted Indoles: Discovery of a Novel, High-Affinity, Selective H5-HT2A Antagonist. Bioorg. Med. Chem. Lett. 2000, 10 (24), 2693-2696. doi: 10.1016/s0960-894x(00)00558-8.
  18. Rabinowitz, M.; Seneci, P.; Rossi, T.; Dal Cin, M.; Deal, M.; Terstappen, G. Solid-Phase/Solution-Phase Combinatorial Synthesis of Neuroimmunophilin Ligands. Bioorg. Med. Chem. Lett. 2000, 10 (10), 1007-1010. doi: 10.1016/s0960-894x(00)00104-9.
  19. Meester, W. J. N.; Rutjes, F. P. J. T.; Hermkens, P. H. H.; Hiemstra, H. Synthesis of Homoallylic Amines via N-Acyliminium Ion Reactions on Solid Support. Tetrahedron Lett. 1999, 40 (8), 1601-1604. doi: 10.1016/s0040-4039(98)02655-0.
  20. Gouilleux, L.; Fehrentz, J.-A.; Winternitz, F.; Martinez, J. Solid Phase Synthesis of Chiral 3-Substituted Quinazoline-2,4-Diones. Tetrahedron Lett. 1996, 37 (39), 7031-7034. doi: 10.1016/0040-4039(96)01541-9.