104739-54-0

Upstream product

• 58581-44-5 2-(Benzylidenamino)propansaeure-methylester-N-oxid 
• 5780-37-0 (E)-acetaldoxime 
• 5445-17-0 Methyl 2-bromopropionate 
• 58581-56-9 (S)-2-Hydroxyamino-propionic acid methyl ester; hydrochloride 
• 872984-87-7 (S)-2-[3-(4-Methoxy-phenyl)-oxaziridin-2-yl]-propionic acid methyl ester 
• 622-33-3 N-benzyloxyamine 

Downstream Products

• 104739-63-1 N-(2-Boc-amino-3-phenylpropyliden)-L-alanin-N-oxid-methylester 

Relevant academic research and scientific papers

Stabilizing factors for vanadium(IV) in amavadin

Six secondary N-hydroxy amino acids (amavadin-based ligands) have been prepared through a strategy with nitrone reduction as its key step. Two of these amino acids are the new amavadin ligand analogues 4a and 4b containing either a phenyl or a benzyl grou

Optically pure N-hydroxy-O-triisopropylsilyl-α-L-amino acid methyl esters from AlCl3-assisted ring opening of chiral oxaziridines by nitrogen containing nucleophiles

This article reports a straightforward and unprecedented process of AlCl3-assisted oxaziridine ring opening by nitrogen containing nucleophiles, in a totally anhydrous milieu. Under these conditions, nucleophiles exclusively attack the carbon atom of the three-membered heterocycles, obtained from methyl esters of natural α-amino acids, generating N-hydroxy-α-L-amino acid methyl esters. No nitrones, amides, or other side products, either from unwanted rearrangements or due to the attack of the nucleophile on the N atom of the oxaziridine systems, are formed. The hydroxylamine compounds are recovered in excellent yields, after their site-specific conversion into the corresponding O-triisopropylsilyl derivatives, by exposure to triisopropylsilyl triflate in the presence of 1H-imidazole. Derivatization, performed immediately after the recovery of the N-hydroxylated precursors, allows the chiral integrity of the asymmetric α-carbon atoms in the amino acid methyl esters to be retained. It also protects the obtained compounds from frame degradation by disproportionation. N-Hydroxy-O- triisopropylsilyl-α-L-amino acid methyl esters are important intermediates in the study of natural α-L-amino acid metabolic pathways and are ideal candidates as starting materials in the synthesis of biologically, pharmacologically, and nutritionally important N-hydroxy peptides.

"Nitrono" Peptides, I. - An Isomeric and Isoelectronic Equivalent of the Peptide Bond

Optically active Boc-α-L-amino aldehydes 1 are converted with N-hydroxy-α-L-amino acid methyl esters 2 into the N-blocked "nitrono" dipeptide esters 3a-l.