125049-95-8

Upstream product

• 125050-15-9 N-(benzyloxy)amide of α-N-carbobenzoxy-δ-hydroxy-D-norvaline 
• 125050-02-4 O-benzyloxime of α-N-carbobenzoxy-γ-aldehyde of D-glutamic acid 
• 125050-13-7 α-N-carbobenzoxy-δ-acetoxy-D-norvaline 
• 250215-08-8 N²-benzyloxycarbonyl-N⁵-(3-phenyloxaziridinyl)-L-ornithine 
• 250215-07-7 N₂-benzyloxycarbonyl-N₅-benzylidene-L-ornithine 
• 2640-58-6 Nα-benzyloxycarbonyl-L-ornithine 
• 100-39-0 benzyl bromide 
• 89969-27-7 (S)-4-(3-Benzyloxyimino-propyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 125049-81-2 (R)-4-(3-Benzyloxyimino-propyl)-5-oxo-oxazolidine-3-carboxylic acid benzyl ester 
• 501-53-1 benzyl chloroformate 
• 5891-45-2 N-benzoyloxycarbonyl L-glutamic acid α-t-butylester 
• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 35418-16-7 L-t-butyl pyroglutamate 
• 124620-51-5 2-Benzyloxycarbonylamino-5-hydroxy-pentanoic acid tert-butyl ester 

Downstream Products

• 162553-90-4 (Bis-N,N'-(Cbz)-L-lysyl-D-threo-β-hydroxyaspartyl β-benzyl ester)-L-alanyl-D-allo-threonyl-L-alanyl-δ-N-(benzyloxy)-D-cycloornithine 

Relevant academic research and scientific papers

A 4-tert-butylcalix[4]arene tetrahydroxamate podand based on the 1-oxypiperidine-2-one (1,2-PIPO-) chelate. Self-assembly into a supramolecular ionophore driven by coordination of tetravalent zirconium or hafnium(iv)

An octadentate tetrahydroxamic calix[4]arene podand incorporating 1-hydroxypiperidine-2-one (1,2-PIPOH) binding units has been designed as a specific chelator for tetravalent metal cations like Zr4+ or Hf 4+. This receptor, which can be considered as the first ever abiotic ligand possessing only cyclic six-membered hydroxamate groups, has been synthesized and characterized in its tetraprotonated form (1H4). Contrary to expectation, however, this new chelator did not form a 1:1 complex upon reaction with M(acac)4 (M = Zr and Hf; acac = acetylacetonate), but rather self-assembled into a dimeric species of 2:2 stoichiometry. The latter could be characterized in solution by mass spectrometry and NMR spectroscopy as its monopotassium adduct ([M2K(1)2] +), pointing to the ionophoric character of the M2(1) 2 complex. This journal is the Partner Organisations 2014.

1-Hydroxy-3-amino-2-piperidone (δ-N-Hydroxycycloornithine) Derivatives: Key Intermediates for the Synthesis of Hydroxamate-Based Siderophores

Several routes for the synthesis of δ-N-(benzyloxy)cycloornithine (2) from glutamic acid derived starting materials are described.Efficient methods were developed for the synthesis of glutamic acid γ-semialdehyde and γ-hydroxynorvaline derivatives as key substrates for the preparation of δ-N-hydroxyornithine analogues.Thus, the best approaches to the synthesis of 2 were: (1) reductive cyclization of an N-hydroxysuccinimide ester of the O-benzyloxime 4 of α-amino-protected glutamic acid γ-semialdehyde 5 and (2) cyclization of the N-(benzyloxy)amide of δ-bromonorvaline (7).