28094-73-7

Usage

Uses

Used in Chemical Synthesis:
(3S)-3-Z-AMINO-1-DIAZO-4-METHYL-2-PENTANONE is used as a reactive intermediate in chemical synthesis for the development of new compounds and materials. Its unique reactivity and structural features make it a valuable component in the synthesis of complex organic molecules.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (3S)-3-Z-AMINO-1-DIAZO-4-METHYL-2-PENTANONE may be employed as a building block or a key intermediate in the synthesis of novel drug candidates. Its specific reactivity and structural attributes could contribute to the discovery of new therapeutic agents with unique mechanisms of action.
Used in Material Science:
(3S)-3-Z-AMINO-1-DIAZO-4-METHYL-2-PENTANONE can be utilized in material science as a component in the development of advanced materials with specific properties. Its incorporation into polymers, coatings, or other materials could lead to the creation of innovative products with improved performance characteristics.

Upstream product

• 186581-53-3 diazomethane 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 119153-86-5 C₁₆H₂₁NO₆ 
• 501-53-1 benzyl chloroformate 
• 1685-33-2 N-[(benzyloxy)carbonyl]-D-valine 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 640-68-6 D-Val-OH 
• 41445-88-9 (2-methylpropoxy)carbonyl N-[(benzyloxy)carbonyl]-D-valinate 
• 72-18-4 L-valine 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 215608-32-5 (R)-3-<(benzyoxycarbonyl)amino>-4-methylpentanoic acid 
• 1258214-04-8 6-(4-(4-((R)-1-(benzyloxycarbonylamino)-2-methylpropyl)thiazol-2-yl)-6-(3-ethylureido)pyridin-3-yl)-1-((S)-1-hydroxy-3,3-dimethylbutan-2-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 1616868-54-2 (R)-S-3-(benzyloxycarbonylamino)-4-methylpentyl ethanethioate 
• 1616868-42-8 (R)-3-(benzyloxycarbonylamino)-4-methylpentyl methanesulfonate 
• 1616868-62-2 (R)-3-benzyloxycarbonylamino-4-methylpentane-1-sulfonic acid 
• 65144-33-4 N-3-carboxypropanoyl-alanyl-alanyl-prolyl-valyl-chloromethylketone 
• 90105-47-8 (S)-1-[(S)-2-((S)-2-Amino-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid ((S)-3-chloro-1-isopropyl-2-oxo-propyl)-amide 
• 288623-03-0 N-carboxy-(S)-3-amino-4-methylpentanoic acid anhydride 

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.

Continuous flow synthesis of β-amino acids from α-amino acids via Arndt-Eistert homologation

A fully continuous four step process for the preparation of β-amino acids from their corresponding α-amino acids utilizing the Arndt-Eistert homologation approach is described. the Partner Organisations 2014.

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.

Complexation of chiral di (N-Protected α-Amino)-β-diketones with some transition metals

Chiral Di (N-protected a-amino)-b-diketones and its transition metal complexes have been synthesized. Di(N-protected a-amino)-b- diketones were prepared by reaction of activation of N-protected- a-amino acids (imidazolide) with a-diazoketones derived from natural amino acids in presence of lithium diisopropyl amid in tetrahydrofuran as a solvent at -78 °C and treatment the product with rhodium acetate to remove diazo group. The synthesized compounds were characterized by analytical techniques viz: IR, NMR and elemental analysis. The thermal stability of the newly synthesized metal complexes have been studied.

Synthesis and characterization of chiral di(N-protected-α-amino) diazo-β-diketones from α-diazoketones and imidazolides derived from amino acids

Di(N-protected-α-amino)diazo-β-diketones were prepared by the reaction of activated N-protected-α-amino acids (imidazolides) with α-diazoketones, derived from natural amino acids, in the presence of lithium diisopropylamide in tetrahydrofuran as the solvent at -78 °C.

Antineoplastic agents. 590. X-ray crystal structure of dolastatin 16 and syntheses of the dolamethylleuine and dolaphenvaline units

Three advances necessary to bring dolastatin 16 (1) into full-scale preclinical development as an anticancer drug have been accomplished. The X-ray crystal structure of dolastatin 16 has been solved, which allowed stereoselective syntheses of its two new

HETEROCYCLIC UREA DERIVATIVES AND METHODS OF USE THEREOF

Compounds of formula (IA) and their pharmaceutically acceptable salts are described. Processes for their preparation, pharmaceutical compositions containing them, their use as medicaments and their use in the treatment of bacterial infections are also described.

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

Total synthesis of N14-desacetoxytubulysin H

Equation presented The N14-desacetoxy analogue of tubulysin H was prepared in 20 steps and 2.1% overall yield. Our strategy features a thiazole anion addition to assemble the tubuvaline residue at the C(10)-C(11) bond, as well as acylations at

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.