339201-37-5Relevant academic research and scientific papers
Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α-hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters
Bouillon, Isabelle,Brosse, Nicolas,Vanderesse, Régis,Jamart-Grégoire, Brigitte
, p. 2223 - 2234 (2007/10/03)
The preparation of chiral orthogonally protected Nα-Z, Nβ-Fmoc- or Boc-α-hydrazinoacids derivatives, directly suitable for SPPS, is described in six steps with good yields starting from the corresponding α-aminoacids. The coupling reaction assays performed in liquid phase between Nα-Z-hydrazinoesters and N-Fmoc-α-aminoacids demonstrated the low reactivity of the hydrazinoester derivatives. However, we found that the acid fluoride method allowed the formation of hydrazinodipeptides almost quantitatively.
Preparation of Multiply Protected Alkylhydrazine Derivatives by Mitsunobu and PTC Approaches
Brosse, Nicolas,Pinto, Maria-Fatima,Jamart-Gregoire, Brigitte
, p. 4757 - 4764 (2007/10/03)
Alkylation reactions of hydrazine derivatives by Mitsunobu or PTC approaches are described. It has been shown that aminophthalimide derivatives are better acidic partners than their aminoimidodicarbonate (NBoc2) analogues, the presence of the phthaloyl group increasing the acidity of the sole proton and concomitantly reducing steric hindrance. Moreover, N-aminophthalimide derivatives can be efficiently converted into the corresponding N-amino-imidodicarbonates by a three-stage, one-flask procedure under very mild conditions. These procedures can also be efficiently used for the preparation of orthogonally Nα,Nβ -diprotected α-hydrazino esters. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
