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Benzotriazol-1-yl Diethyl Phosphate and Benzotriazol-1-yl Diphenyl Phosphate. New Convenient Reagents for the Peptide Synthesis

  • Kim, Sung-Gak (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Chang, He-Ung (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Ko, Young-Kwan (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1987.12.20

Abstract

Benzotriazol-1-yl Diethyl phosphate and benzotriazol-1-yl diphenyl phosphate were conveniently prepared in essentially quantitative yields by the reaction of diethyl chlorophosphate and diphenyl chlorophosphate with equal amounts of 1-hydroxybenzotriazole and triethylamine in tetrahydrofuran at room temperature, respectively. Benzotriazol-1-yl diethylphosphate was effective for the preparation of amides from carboxylic acids amines. Young test and Anderson test for racemization studies using benzotriazol-1-yl diethyl phosphate were investigated and practically no racemization occurred. However, racemization occurred to some extent during coupling of Z-Phe-Val-OH with Pro-OBu. Several dipeptides and tripeptides were prepared without little racemization using benzotriazol-1-yl diethyl phosphate. Benzotriazol-1-yl diphenyl phosphate was less effective than benzotriazol-1-yl diethyl phosphate in terms of the degree of racemization.

Keywords

References

  1. Org. React. (N. Y.) v.12 N. F. Albertson
  2. Acc. Chem. Res. v.2 D. S. Tarbell
  3. The Peptides, Analysis, Synthesis, Biology v.1 E. Gross;J. Meienhofer(eds.)
  4. Tetrahedron Lett. S. Yamada;Y. Takeuchi
  5. Tetrahedron v.32 T. Shioiri;Y. Yokoyama;Y. Kasai;S. Yamada
  6. Tetrahedron Lett. A. G. Jackson;G. W. Kenner;G. A. Moor;R. Ramage;W. D. Thorpe
  7. Synthesis S. Bernasconi;A. Comini;A. Corbella;M. Sisti
  8. J. Am. Chem. Soc. v.107 R. D. Tung;D. H. Rich
  9. J. Am. Chem. Soc. v.94 T. Shioiri;K. Ninomiya;S. Yamada
  10. Synthesis A. Gorecka;M. Leplawy;J. Zabrocki;A. Zwierzak
  11. Tetrahedron Lett. H. Ogura;S. Nagai;K. Takeda
  12. J. C. S. Chem. Comm. Y. Kiso;T. Miyazaki;M. Satomi;H. Hiraiwa;T. Akita
  13. Chem. Lett. M. Miyake;M. Kirisawa;N. Tokutake
  14. Synthesis M. Ueda;H. Oikawa;T. Teshirogi
  15. J. Org. Chem. v.50 K. Takeda;K. Tsuboyama;K. Yamaguchi;H. Ogura
  16. J. C. S. Chem. Comm. S. Kim;H. Chang
  17. Bull. Korean Chem. Soc. v.7 H. Chang;S. Kim
  18. Nucl. Acids Res. v.10 G. A. van der Marel;C. A. A. van Boeckel;G. Wille;J. H. van Boom
  19. Tetrahedron Lett. C. T. J. Wreesman;A. Fidder;G. H. Veeneman;G. A. van der Marel;J. H. van Boom
  20. Tetrahedron Lett. B. Castro;J. R. Dormoy;G. Evin;C. Selve
  21. Tetrahedron Lett. S. Kim;J. I. Lee;Y. K. Ko
  22. J. C. S. Chem. Comm. S. Kim;S. S. Kim
  23. J. Org. Chem. v.51 S. Kim;K. Y. Yi
  24. Tetrahedron Lett. S. Kim;H. Chang;Y. K. Ko
  25. Tetrahedron Lett. S. Yamada;Y. Kasai;T. Shioiri
  26. J. Chem. Soc. M. W. Williams;G. T. Young
  27. J. Am. Chem. Soc. v.74 G. W. Anderson;R. W. Young
  28. J. Am. Chem. Soc. v.89 G. W. Anderson;J. E. Zimmermann;F. M. Callanan
  29. Chem. Pharm. Bull. v.30 S. Takuma;Y. Hamada;T. Shioiri
  30. Chem. Pharm. Bull. v.22 Y. Takeuchi;S. Yamada
  31. Tetrahedron Lett. T. Mukaiyama;R. Matsueda;M. Suzuki
  32. Chem. Lett. Y. Watanabe;N. Morito;K. Kamekawa;T. Mukaiyama
  33. Chem. Ber. v.108 R. Appel;G. Baumann;W. Struver
  34. J. Org. Chem. v.26 W. D. Cash
  35. J. Chem. Soc., (C) K. Lloid;G. T. Young
  36. J. Am. Chem. Soc. v.82 G. W. Anderson;R. Paul
  37. Synthesis V. Dourtoglou;B. Gross
  38. J. Org. Chem. v.33 D. E. Nitecki;B. Halpern;J. W. Westley

Cited by

  1. ChemInform Abstract: Benzotriazol‐1‐yl Diethyl Phosphate and Benzotriazol‐1‐yl Diphenyl Phosphate. New Convenient Reagents for the Peptide Synthesis. vol.19, pp.23, 1987, https://doi.org/10.1002/chin.198823308
  2. Amide bond formation: beyond the myth of coupling reagents vol.38, pp.2, 1987, https://doi.org/10.1039/b701677h
  3. Design and Synthesis of New 4-Alkylthio Monocyclic β-Lactams vol.34, pp.1, 1987, https://doi.org/10.5012/bkcs.2013.34.1.121