160056-97-3Relevant academic research and scientific papers
Solid phase synthesis of hydroxamic acids
Dankwardt, Sharon M.
, p. 761 - 761 (1998)
The solid phase synthesis of hydroxamic acids is presented. Carboxylic acid ester linked, polymer-supported CBZ-protected amino acids were displaced from the resin with aqueous hydroxylamine to provide the corresponding hydroxamic acids.
Organocatalytic Multicomponent Synthesis of α/β-Dipeptide Derivatives
Martzel, Thomas,Annibaletto, Julien,Millet, Pierre,Pair, Etienne,Sanselme, Morgane,Oudeyer, Sylvain,Levacher, Vincent,Brière, Jean-Fran?ois
supporting information, p. 8541 - 8545 (2020/06/24)
A straightforward multicomponent Knoevenagel-aza-Michael-cyclocondensation reaction involving readily available hydroxamic acid-derived from naturally occurring α-amino acids allows a diversity-oriented synthesis of novel isoxazolidin-5-ones possessing an N-protected α-amino acid pendant with good to high diastereoselectivities thanks to a match effect with a chiral organocatalyst. These diversely substituted heterocycles, easily isolated as a single diastereoisomer, proved to be versatile platforms for the formation of an array of α/β-dipeptide fragments.
Racemization free longer N-terminal peptide hydroxamate synthesis on solid support using ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate
Manne, Srinivasa Rao,Thalluri, Kishore,Giri, Rajat Subhra,Paul, Ashim,Mandal, Bhubaneswar
supporting information, p. 6108 - 6111 (2015/10/28)
A facile, efficient, racemization-free, and environment friendly protocol for the synthesis of peptide hydroxamic acids directly from carboxylic/amino acids by ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate in the presence of DIPEA/DMAP at room temperature is described. The compatibility of this method with Fmoc based solid phase peptide synthesis (SPPS) is also demonstrated by synthesizing three relatively large N-terminal peptide hydroxamic acids on resin. Also, some biologically important hydroxamates are synthesized using this protocol.
1-propanephosphonic acid cyclic anhydride (T3P) as an efficient promoter for the Lossen rearrangement: Application to the synthesis of urea and carbamate derivatives
Vasantha, Basavalingappa,Hemantha, Hosahalli P.,Sureshbabu, Vommina V.
experimental part, p. 2990 - 2996 (2010/10/21)
The synthesis of hydroxamic acids starting from carboxylic acids employing 1-propanephosphonic acid cyclic anhydride (T3P) activation is described. Application of ultrasonication accelerates this conversion. Further, the T3P has also been employed to activate the hydroxamates, leading to isocyanates via the Lossen rearrangement. The isocyanates were trapped with suitable nucleophiles to afford the corresponding ureas and carbamates. Georg Thieme Verlag Stuttgart New York.
Simple one-flask method for the preparation of hydroxamic acids
Giacomelli, Giampaolo,Porcheddu, Andrea,Salaris, Margherita
, p. 2715 - 2717 (2007/10/03)
(Matrix presented) A one-step conversion of carboxylic acids to hydroxamic acids under very mild conditions is described. This simple and efficient method has been applied for the synthesis of enantiopure hydroxamate of α-amino acids and peptides.
Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions
Ritter, Allen R.,Miller, Marvin J.
, p. 4602 - 4611 (2007/10/02)
The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected α-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions.The cycloaddition reactions afforded synthetically useful qu
