944913-87-5

Upstream product

• 13139-28-1 (S)-N-benzyloxycarbonylvalinamide 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 100-39-0 benzyl bromide 
• 17343-55-4 (S)-N-benzyloxycarbonyl-2-amino-isopentanenitrile 
• 119153-86-5 C₁₆H₂₁NO₆ 
• 501-53-1 benzyl chloroformate 
• 72-18-4 L-valine 

Downstream Products

• 944913-91-1 (S)-1-benzyl-4-[(Z)-tert-butyloxycarbonylmethylidene]-5-(1-methylethyl)-imidazolidin-2-one 
• 1263315-48-5 benzyl (2S,3R)-2-isopropyl-5-oxopyrrolidin-3-ylcarbamate 
• 1263315-49-6 (2S,3R)-tert-butyl 3-(benzyloxycarbonylamino)-2-isopropyl-5-oxopyrrolidine-1-carboxylate 
• 1263315-51-0 (3R,4S) 3-(benzyloxycarbonylamino)-4-(tertbutoxycarbonylamino)-5-methylhexanoic acid 
• 1415109-61-3 C₂₆H₄₁N₃O₇ 
• 1415109-63-5 C₂₁H₃₃N₃O₅ 
• 1415109-66-8 C₂₉H₄₆N₄O₈ 
• 1415109-69-1 C₃₂H₅₂N₄O₈ 
• 1415109-71-5 C₃₅H₅₀N₄O₈ 
• 944914-05-0 (4S,5S)-4-(2-hydroxyethyl)-5-(1-methylethyl)-1-phenylmethyl-imidazolidin-2-one 
• 944913-95-5 (4R,5S)-5-(1-methylethyl)-1-phenylmethyl-2-oxo-imidazolidin-4-acetic acid tert-butyl ester 

Relevant academic research and scientific papers

Original β,γ-diamino acid as an inducer of a γ-turn mimic in short peptides

Original αγα tripeptides containing one β,γ-diamino acid have been synthesized and their conformation determined by extensive NMR and molecular dynamic studies. These studies revealed the presence of a C9 hydrogen bonded turn around the β,γ-diamino acid which was stabilized by bulky side chains of the preceding residue. This turn can be considered as a mimic of the well-known γ-turn. The Royal Society of Chemistry 2012.

AmIno Acid Homologation by the Blaise Reaction: A new entry into nitrogen heterocycles

(Chemical Equation Presented) A general strategy for the amino acid homologation via Blaise reaction and subsequent reduction is presented. This strategy involves the preparation of protected α-amino nitriles from the corresponding amino acids, followed by the zinc-mediated condensation of tert-butyl bromoacetate, to give the imidazolidones after iminozincate cyclization. Reduction gave the saturated imidazolidinones with cis or trans stereochemistry, depending on the reduction conditions. This strategy was applied to nonfunctionalized amino acids and to functionalized amino acids such as serine and aspartic acid. Additionally, acidic hydrolysis of cis or trans imidazolidinones to the corresponding chiral 4-aminopyrrolidones is described.

A Stereoselective entry into functionalized 1,2-diamines by zinc-mediated homologation of α-aminoacids

A general, stereoselective synthsis of 4,5-disubstituted imidazolidines-2-ones from α-aminoacids has been developed: the key steps are a Biaise reaction of bromoacetate on α-aminonitriles and further reduction. Although reduction with sodium cyanoborohydride afforded a mixture of cis and trans isomers 6a-e with moderate to good stereoselectivity, reduction with sodium in liquid ammonia gave the trans isomers 8a-e with complete stereoselectivity. Acidic hydrolysis of the urea gave 4-amino-pyrrolidinones, which can be precursors to β,γ-diaminoacids or 3-aminopyrrolidines.