Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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t-Butyl Benzotriazol-1-yl Carbonate and Benzyl Benzotriazol-1-yl Carbonate. Now Reactive Amino Protective Reagents for t-Butoxycarbonylation and Benzyloxycarbonylation of Amines and Amino Acids

  • Kim, Sung-Gak (Department of Chemistry, Korea Advanced Institute of Science and Technology) ;
  • Chang, Heung (Department of Chemistry, Korea Advanced Institute of Science and Technology)
  • Published : 1986.02.20
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Abstract

New amino protective reagents, t-butyl benzotriazol-1-yl carbonate and benzyl benzotriazol-1-yl carbonate, for t-butoxycarbonylation and benzyloxycarbonylation of amines and amino acids have been developed. t-Butyl benzotriazol-1-yl carbonate reacts rapidly and cleanly with various amines and amino acids to afford N-Boc amines and N-Boc amino acids in high yields and benzyl benzotriazol-1-yl carbonate is also found to be very effective in the benzyloxycarbonylation of amino acids.

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References

  1. The Peptides, Analysis, Synthesis, Biology E, Gross;J. Meienhofer
  2. Protective Groups in Organic Synthesis T.W. Greene
  3. J. Am. Chem. Soc. v.70 A.R. Choppine;J.W. Rogers
  4. Helv. Chim. Acta v.42 R. Schwyzer;P. Sieber;H. Kappeler
  5. Proc. Nat. Acad. Sci. USA v.69 D.S. Tarbell;Y. Yamamoto;B.M. Pope
  6. Bull. Chem. Soc. Jap. v.50 M. Itoh;D. Hagiwara;T. Kamiya
  7. J. Chem. Soc., Chem. Commun. E. Guibe-Jampel;M. Wakselman
  8. Tetrahedron Lett. M. Frankel;D. Ladkany;C. Gilon;Y. Wolman
  9. Angew. Chem. Int. Ed. Engl. v.6 H. Gross;L. Bilk
  10. Tetrahedron Lett. E. Guibe-Jampel;G. Bram;M. Vilkas
  11. Tetrahedron Lett. T. Kunieda;T. Higuchi;Y. Abe;M. Hirobe
  12. J. Org. Chem. v.47 Y. Kita;J. Haruta;H. Yasuda;K. Fukunaga;Y. Shirouchi;Y. Tamura
  13. Tetrahedron Lett. R.B. Harris;I.B. Wilson
  14. Chem. Lett. S. Kim;J.I. Lee
  15. Tetrahedron Lett. S. Kim;H. Chang;Y.K. Ko
  16. Tetrahedron Lett. S. Kim;K.Y. Yi
  17. J. Chem. Soc., Chem. Commun. S. Kim;Y.K. Ko
  18. J. Org. Chem. v.50 S. Kim;H. Chang;W.J. Kim
  19. Bull. Korean Chem. Soc. v.6 S. Kim;Y.K. Ko
  20. J. Chem. Soc., Chem. Commun. S. Kim;H. Chang
  21. Bull. Chem. Soc. Jap. v.37 H. Otsuka;K. Inouye
  22. J. Am. Chem. Soc. v.81 K. Hoffmann;R. Schmiechen;R.D. Wells;Y. Wolmann;N. Yanaihara
  23. Liebig Ann. Chem. v.702 E. Schnabel
  24. Bull. Chem. Soc. Jpn. v.46 T. Nagasawa;K. Kuroiwa;K. Narita;Y. Isowa
  25. Bull. Chem. Soc. Jpn. S. Kim;J.I. Lee;K.Y.Yi
  26. J. Am. Chem. Soc. v.79 K. Hoffmann;A. Johl;A.E. Furlenmeier;H. Kappeler
  27. J. Am. Chem. Soc. v.79 H. Schwarz;F.M. Bumpus;I.H. Page
  28. Chem. Ber. v.91 W. Grassmann;E. Wunsch;A. Riedel
  29. J. Biol. Chem. v.232 R.B. Merrifield
  30. Bull. Chem. Soc. Jpn. v.31 F. Sakiyama;K. Okawa;T. Yamakawa;S. Akabori
  31. Z. Naturforsch v.206 H. Voss
  32. Bull. Chem. Soc. Jpn. v.39 S. Sakakibara;M. Fujino

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