Bulletin of the Korean Chemical Society

  • 제8권6호
  • /
  • Pages.471-475
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  • 1987
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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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)
  • 발행 : 1987.12.20
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초록

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.

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참고문헌

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피인용 문헌

  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