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Volumn , Issue 20, 1999, Pages 2871-2874

Nu-Alloc temporary protection in solid-phase peptide synthesis. the use of amine-borane complexes as allyl group scavengers

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EID: 0001561005     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906025a     Document Type: Article
Times cited : (74)

References (27)
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    • 1994, 35, 4349; R. Beugelmans, L. Neuville, M. Bois-Choussy, J. Chastanet and J. Zhu, Tetrahedron Lett., 1995,36, 3129.
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    • 1997, 53, 4957; K. Burgess and M.J. Ohlmeyer, Chem. Rev., 1991,91, 1179.
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  • 22
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    • note 2 mol% of Pd(PPh3)4, half-reaction times of less than 5 min at room temperature were found, in our laboratory, for the conversion of the Alloc derivatives of morpholine or Nmethylbenzylamine to the corresponding allylamines. As a comparison, the half-conversion times for Alloc-Val-OMe or Alloc-Tyr(O-f-Bu)-OMe under similar conditions are approximatively 1 h.
    • In the presence of 2 mol% of Pd(PPh3)4, half-reaction times of less than 5 min at room temperature were found, in our laboratory, for the conversion of the Alloc derivatives of morpholine or Nmethylbenzylamine to the corresponding allylamines. As a comparison, the half-conversion times for Alloc-Val-OMe or Alloc-Tyr(O-f-Bu)-OMe under similar conditions are approximatively 1 h.
  • 24
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    • The concentration of reactants in these control experiments were the same as those used in the deprotection of N"-Alloc derivatives 3 and 4.
    • The concentration of reactants in these control experiments were the same as those used in the deprotection of N"-Alloc derivatives 3 and 4.


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