102123-81-9

Usage

Uses

Used in Organic Synthesis:
(S)-3-Z-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is used as a reagent in the field of organic synthesis for the creation of various chemicals and pharmaceuticals. Its unique structure allows for versatile reactions and the formation of a wide range of products.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (S)-3-Z-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is used as a key intermediate in the synthesis of specific drug molecules. Its ability to participate in various chemical reactions makes it a valuable compound for developing new medications with potential therapeutic applications.
Used in Chemical Research:
(S)-3-Z-AMINO-1-DIAZO-5-METHYL-2-HEXANONE is also employed in chemical research to study the properties and reactivity of diazo compounds. Understanding the behavior of such compounds can lead to the development of new synthetic methods and the discovery of novel chemical entities with potential applications in various fields.

Upstream product

• 186581-53-3 diazomethane 
• 2018-66-8 Z-Leu-OH 
• 102123-80-8 C₁₉H₂₇NO₆ 
• 501-53-1 benzyl chloroformate 
• 61-90-5 L-leucine 
• 148854-04-0 (C₈H₇O₂)(NHCHCOO)(CH₂C₃H₇)(CO₂C₂H₅) 

Downstream Products

• 118252-77-0 (3S)-3-<(benzyloxycarbonyl)amino>-1-bromo-5-methyl-2-oxohexane 
• 52467-54-6 Cbz-leucyl chloromethane 
• 118247-68-0 N-Benzyloxycarbonyl-L-Homoleucine 
• 96386-95-7 [(S)-1-(2-Hydroxy-ethyl)-3-methyl-butyl]-carbamic acid benzyl ester 
• 1616868-55-3 (S)-S-3-(benzyloxycarbonylamino)-5-methylhexyl ethanethioate 
• 1616868-44-0 (S)-3-(benzyloxycarbonylamino)-5-methylhexyl methanesulfonate 
• 96386-94-6 methyl (S)-3-(benzyloxycarbonylamino)-5-methylhexanoate 
• 1616868-63-3 (S)-3-benzyloxycarbonylamino-5-methylhexane-1-sulfonic acid 
• 93092-75-2 (S)-5-Benzyloxycarbonylamino-7-methyl-4-oxo-octanoic acid 
• 118247-76-0 Z-β-homo-Leu-D-Asp(OBzl)-NHCH2CH2C6H5 
• 118247-70-4 (Benzyloxycarbonyl)-β-homo-L-leucyl-β-benzyl-L-aspartic acid 2-phenylethylamide 
• 118247-75-9 Z-β-homo-Leu-D-Asp(OBzl)-NHCH2C6H5 
• 118247-69-1 Z-β-homo-Leu-Asp(OBzl)-NHCH2C6H5 

Relevant academic research and scientific papers

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Synthesis of enantiopure free and N-benzyloxycarbonyl-protected 3-substituted homotaurines from naturally occurring amino acids

Enantiopure N-benzyloxycarbonyl-protected and free 3-substituted homotaurines were synthesized from naturally occurring amino acids via N-benzyloxycarbonyl protection, Arndt-Eistert homologation, reduction, esterification with thioacetic acid, and oxidation with performic acid. The current method is a convenient, practical, and salt-free method for the synthesis of enantiopure 3-substituted homotaurine with moderate to good yields.

Facile synthesis of optically active imidazole derivatives

Five optically active imidazole derivatives have been synthesized via a facile 4-step reaction sequence starting from commercially available and inexpensive N-Cbz amino acids. While microwave assisted condensation was unsuccessful, the condensation of the

Effective methods for the synthesis of N-methyl β-amino acids from all twenty common α-amino acids using 1,3-oxazolidin-5-ones and 1,3-oxazinan-6-ones

N-Methyl β-amino acids are generally required for application in the synthesis of potentially bioactive modified peptides and other oligomers. Previous work highlighted the reductive cleavage of 1,3-oxazolidin-5-ones to synthesise N-methyl α-amino acids. Starting from α-amino acids, two approaches were used to prepare the corresponding N-methyl β-amino acids. First, α-amino acids were converted to N-methyl α-amino acids by the so-called '1,3-oxazolidin-5-one strategy', and these were then homologated by the Arndt-Eistert procedure to afford N-protected N-methyl β-amino acids derived from the 20 common α-amino acids. These compounds were prepared in yields of 23-57% (relative to N-methyl α-amino acid). In a second approach, twelve N-protected α-amino acids could be directly homologated by the Arndt-Eistert procedure, and the resulting β-amino acids were converted to the 1,3-oxazinan-6-ones in 30-45% yield. Finally, reductive cleavage afforded the desired N-methyl β-amino acids in 41-63% yield. One sterically congested β-amino acid, 3-methyl-3-aminobutanoic acid, did give a high yield (95%) of the 1,3-oxazinan-6-one (65), and subsequent reductive cleavage gave the corresponding AIBN-derived N-methyl β-amino acid 61 in 71% yield (Scheme 2). Thus, our protocols allow the ready preparation of all N-methyl β-amino acids derived from the 20 proteinogenic α-amino acids.

Chiral imidazole derivatives synthesis from enantiopure N-protected α-amino acids

A route to the preparation of enantiopure ligands based on a 2-phenylimidazol ring is described. The stereogenic centre is placed into the chain bonded to the fourth carbon of the imidazole ring. The synthesis starts from inexpensive and readily available

Convenient and simple homologation of Nα-urethane protected α-amino acids to their β-homologues with concomitant o-nitrophenylesters formation

The Wolff rearrangement of α-aminodiazoketones derived from Nα-urethane protected α-amino acids in presence of o-nitrophenol catalyzed by silver acetate at low temperature is described. The potential utility of the well-known ketene intermediat

Synthesis of optically active β-amino acid N-carboxyanhydrides

(Equation presented) Methodology has been developed for the general synthesis of optically active β-amino acid N-carboxyanhydrides (β-NCAs) through cyclization of Nβ-Boc or Nβ-Cbz β-amino acids using phosphorus tribromide. The format

Convenient in situ synthesis of nonracemic N-protected β-amino aldehydes from β-amino acids. Applications in Wittig reactions and heterocycle synthesis

N-Z-γ-amino alcohols derived from nonracemic β-amino acids are smoothly oxidised by manganese dioxide in acetonitrile to afford aldehydes which can be trapped in situ in Wittig reactions with carbonyl-substituted phosphoranes. The application of this methodology to the synthesis of the alkaloids (S)-(+)-N-BOC-coniine, (S)-(-)-coniceine and a pipecoline precursor is described.

Stereocontrolled synthesis of erythro N-protected α-amino epoxides and peptidyl epoxides

N-protected α-amino epoxides of erythro configuration, derived from α-amino acids, were synthesized in a stereoselective manner. The erythro (2S,3S), configuration was achieved by the synthetic sequence: amino acid -> haloketone -> halohydrin -> epoxide. A mechanistic explanation for the observed stereoselectivity is presented. This stereoselective synthetic approach was applied to the synthesis of a variety of short peptidyl epoxides, bearing a predefined absolute configuration of the chiral epoxide moiety.

Renin inhibitors containing isosteric replacements of the amide bond connecting the P3 and P2 sites

Renin inhibitors having 13 different isosteres connecting the P3 and P2 positions have been prepared. Synthetic routes and in vitro activity exhibited by these compounds are discussed. The two most potent compounds, 47 and 48, contai