1663-47-4

Usage

Uses

Used in Pharmaceutical Industry:
Methyl (S)-2,5-dioxooxazolidine-4-propionate is utilized as a key intermediate in the synthesis of various drugs and biologically-active substances. Its unique stereochemistry and structural features make it a valuable component in the development of new pharmaceuticals with improved efficacy and selectivity.
Used in Drug Synthesis:
Methyl (S)-2,5-dioxooxazolidine-4-propionate serves as a crucial building block for the creation of novel compounds with potential therapeutic effects. Its incorporation into drug molecules can enhance their pharmacological properties, leading to the discovery of new treatments for various diseases and conditions.
Used in Chiral Synthesis:
Due to its chiral nature, methyl (S)-2,5-dioxooxazolidine-4-propionate is employed in chiral synthesis, where the stereochemistry of a compound plays a significant role in its biological activity. methyl (S)-2,5-dioxooxazolidine-4-propionate can be used to create enantiomerically pure drugs, ensuring optimal therapeutic effects and minimizing potential side effects associated with the less active enantiomer.

InChI:InChI=1/C7H9NO5/c1-12-5(9)3-2-4-6(10)13-7(11)8-4/h4H,2-3H2,1H3,(H,8,11)/t4-/m0/s1

Upstream product

• 4652-65-7 (S)-2-Benzyloxycarbonylamino-pentanedioic acid 5-methyl ester 
• 1499-55-4 L-glutamic acid 5-methyl ester 
• 503-38-8 trichloromethyl chloroformate 
• 56-86-0 L-glutamic acid 
• 75-44-5 phosgene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 6525-53-7 L-glutamic acid dimethyl ester 
• 67-56-1 methanol 
• 27025-22-5 D-glutamic acid-5-methyl ester; hydrochloride 
• 3077-51-8 γ-methyl L-glutamate hydrochloride 

Downstream Products

• 54745-18-5 3-[(S)-3-(2-nitro-phenylsulfanyl)-2,5-dioxo-oxazolidin-4-yl]-propionic acid methyl ester 
• 70830-50-1 (S)-methyl 4,5-diamino-5-oxopentanoate 

Relevant academic research and scientific papers

Preparation of a novel aggregate like sugar-ball micelle composed of poly(methylglutamate) and poly(ethyleneglycol) modified by lactose and its molecular recognition by lectin

We report the preparation and characteristics of a novel micellar aggregate of an amphiphilic diblock copolymer, poly(methylglutamate) (PMG)-poly(ethyleneglycol) (PEG), whose terminus was modified by lactose lactone (LA). Due to the terminal LA moiety, th

Using hydrogen-bonding interactions to control the peptide secondary structures and miscibility behavior of poly(l -glutamate)s with phenolic resin

We synthesized three low-molecular-weight poly(glutamate)s-poly(γ- methyl l-glutamate) (PMLG), poly(γ-ethyl l-glutamate) (PELG), and poly(γ-benzyl l-glutamate) (PBLG)-through living ring-opening polymerization of their α-amino acid-N-carboxyanhydride derivatives and then blended them with phenolic resin to control the secondary structures of these polypeptides. Each of the three binary blends exhibited a single glass transition temperature (differential scanning calorimetry) and a single-exponential decay of proton spin-lattice relaxation times in the rotating frame [T1ρH; solid state nuclear magnetic resonance (NMR) spectroscopy], characteristic of a miscible system. The strength of the interassociative interactions depended on the nature of the hydrogen bond acceptor groups, increasing in the order phenolic/PELG > phenolic/PMLG > phenolic/PBLG, as evidenced through analyses using Fourier transform infrared (FTIR) spectroscopy and the Painter-Coleman association model. The fractions of α-helical conformations (measured using FTIR and solid-state NMR spectroscopy) of PMLG and PELG decreased initially upon increasing the phenolic content but increased thereafter; in contrast, the fraction of α-helical conformations of PBLG increased continuously upon increasing the phenolic contents. Using variable-temperature infrared spectroscopy to investigate the changes in the conformations of the secondary structures of the peptide segments in these three binary blends, we found that the α-helical conformation in these three blend systems correlated strongly with the rigidity of side-chain groups, the strength of the intermolecular hydrogen bonding with the phenolic resin, the compositions of phenolic resin, and the temperature. More interestingly, the content of α-helical conformations of the polypeptides in these phenolic/PBLG blends increased upon increasing the temperature.

PROCESSES FOR PREPARATION OF (S)-TERT-BUTYL 4,5-DIAMINO-5-OXOPENTANOATE

Provided are processes for the preparation of (S)-tert-butyl 4,5-diamino-5-oxopentanoate, or a salt, solvate, hydrate, enantiomer, mixture of enantiomers, or isotopologue thereof. Also provided are solid forms of various intermediates and products obtained from the processes.

PROCESS FOR THE PREPARATION OF N-CARBOXYANHYDRIDES

The invention relates to a process for the preparation of N-carboxyanhydrides by reaction of the corresponding amino acid with phosgene, diphosgene and/or triphosgene in a solvent medium, characterized in that the reaction is a least partially carried out in the presence of an unsaturated organic compound which has one or more ethylenic double bonds. The N-carboxyanhydrides are thus obtained with better yields and an improved purity.

The Synthesis of the High-Potency Sweetener, NC-00637. Part 3: The Glutamyl Moiety and Coupling Reactions

The synthesis of the high-potency sweetener, NC-00637 (1), required selective preparation of the γ-protected glutamic acid. Coupling of the three components could be performed in any order, but the final route involved N-acylation of the protected L-glutamic acid with the acid chloride derived from (S)-2-methylhexanoic acid. Activation of the α-carboxyl group allowed condensation with 5-amino-2-cyanopyridine (4). Saponification of the γ-ester 19 then provided the sweetener 1.

Friedel-Crafts α-aminoacylation of aromatic compounds with a chiral N- carboxy-α-amino acid anhydride (NCA); Part 2

The N-carboxy-α-amino acid anhydrides (NCA) derived from L-Asp(OEt), L- Glu(OMe), L-Met, and L-Pro reacted with aromatic compounds (toluene or benzene) in the presence of AlCl3 to afford the corresponding α-aminoalkyl aryl ketones as hydrochloride salts in moderate yields. The β- and γ-amino acid esters, which were obtained from the reaction of the aromatic compounds with L-Asp(OEt)- and L-Glu(OMe)-NCA, were hydrolyzed by hydrochloric acid to the corresponding β- and γ-amino acids as hydrochloride salts. L-Phe-NCA did not react with benzene in the presence of AlCl3, instead an intramolecular acylation occurred to afford (S)-2-aminoin-danone hydrochloride. The chiralities of the original L-α-amino acids were most retained during these α-aminoacylation.