151121-34-5

Upstream product

• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 91229-91-3 tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate 

Downstream Products

• 151028-17-0 (S)-5-Oxo-4-[1-phenyl-meth-(E)-ylidene]-pyrrolidine-1,2-dicarboxylic acid di-tert-butyl ester 
• 138858-47-6 tert-butyl (2S,4S)-N-(tert-butoxycarbonyl)-4-benzylpyroglutamate 
• 172298-83-8 tert-butyl (2S)-2-tert-butoxycarbonylamino-3-(2-phenyl-4-oxo-pyrimidin-5-yl)propionate 
• 1252661-50-9 di-tert-butyl (2S,4Z)-4-[(4-methylanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-48-5 di-tert-butyl (2S,4E)-4-anilinomethylidene-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-49-6 di-tert-butyl (2S,4Z)-4-[(3-methylanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-52-1 di-tert-butyl (2S,4E)-4-[(4-hydroxyanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-51-0 di-tert-butyl (2S,4E)-4-[(3-hydroxyanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-55-4 di-tert-butyl (2S,4E)-4-[(4-bromoanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-53-2 di-tert-butyl (2S,4Z)-4-[(3-methoxyanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-54-3 di-tert-butyl (2S,4Z)-4-[(3-bromoanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-57-6 di-tert-butyl (2S,4E)-4-[(4-nitroanilino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate 
• 1252661-63-4 (2S,4E)-4-(4-hydroxyanilinomethylidene)pyroglutamic acid hydrochloride 
• 1252661-67-8 (2S,4E)-4-(3-nitroanilinomethylidene)pyroglutamic acid hydrochloride 

Relevant academic research and scientific papers

Parallel solution-phase synthesis of (2S,4E)-4-(arylaminomethylidene) pyroglutamic acids

A library of twelve N(4')-substituted di-tert-butyl (2S,4E)-4- arylaminomethylidene-5-oxopyrrolidine-1,2-dicarboxylates 6/6'a-l were prepared in 47-90% yield by parallel acid-catalysed treatment of di-tert-butyl (2S,4E)-4-[(dimethylamino)methylidene]-5-oxopyrrolidine-1,2-dicarboxylate (4) with anilines 5a - j, ethyl glycinate (5k), and ethyl β-alaninate (31). Acidolytic deprotection of compounds 6a - c, e - j afforded the corresponding (2S,4E)-4-arylaminomethylidene-5-oxopyrrolidine-2-carboxylic acids 7a - c, e - j in 39-99% yield. The configuration around the C=C double bond in the enaminones 6 and 7 was determined by NMR spectroscopy.

Synthesis of 1,2-dithiolane analogues of leucine for potential use in peptide chemistry.

[reaction: see text]1,2-Dithiolanes present several points of interest for both peptide and medicinal chemistry, yet no chiral alpha-amino acids containing this five-membered heterocyclic system are available. We report here the first synthesis of N- and C-protected derivative of (S)-2-amino-3-(1,2-dithiolan-4-yl)propionic acid (Adp) and its 1,3-dithiolic form.

Stereospecific synthesis of (2S,4R)-[5,5,5-2H3]leucine

The first stereospecific chemical synthesis of a sample of the amino acid (2S)-leucine labelled in one of the diastereotopic methyl groups has been achieved using (2S)-pyroglutamic acid as a chiral template. This has been used to develop a method for assigning resonances to the diastereotopic methyl groups of the leucine residues in the 1H NMR spectra of proteins.