26334-33-8

Usage

Uses

Used in Organic Synthesis:
(R,S)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE is used as a chiral auxiliary for controlling the stereochemistry of reactions, enabling the selective formation of one enantiomer over the other. This application is vital in the synthesis of enantiomerically pure compounds, which are often required for biological activity and pharmaceutical development.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, (R,S)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE is employed as a key intermediate in the synthesis of various drugs and complex organic molecules. Its ability to control stereochemistry makes it a valuable tool in the development of new medications with improved efficacy and reduced side effects.
Used in Research and Development:
(R,S)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE is also utilized in research and development settings, where it aids scientists in understanding the effects of stereochemistry on molecular interactions and biological activities. This knowledge can be applied to design more effective drugs and optimize existing ones.
Used in Chemical Education:
As a compound with a chiral center, (R,S)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE serves as an educational tool in teaching the principles of stereochemistry and the importance of enantiomers in organic chemistry and pharmaceutical science. It can be used in laboratory exercises and demonstrations to illustrate these concepts.

InChI:InChI=1/C7H11NO3/c1-4(2)3-5-6(9)11-7(10)8-5/h4-5H,3H2,1-2H3,(H,8,10)

Upstream product

• 75-44-5 phosgene 
• 328-38-1 (R)-leucine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 114488-94-7 H-D-Leu-OH 
• 503-38-8 trichloromethyl chloroformate 
• 61-90-5 L-leucine 

Downstream Products

• 7298-84-2 Leu-Ala 
• 462-60-2 N-carbamoylglycine 
• 686-50-0 L-leucyl-glycine 
• 61-90-5 L-leucine 
• 3063-05-6 Leu-Phe-OH 

Relevant academic research and scientific papers

Sheddable micelles based on disulfide-linked hybrid PEG-polypeptide copolymer for intracellular drug delivery

A novel reduction-sensitive sheddable micelle based on disulfide-linked hybrid PEG-polypeptide mPEG-SS-Pleu was demonstrated for intracellular drug delivery. These micelles are composed of an mPEG shell and polypeptide core, characterized by FT-IR, 1H NMR, fluorescence techniques, TEM, and DLS. Interestingly, they would undergo a fast sheddable process when encounter the reduction sensitive condition, indicated by the aggregation phenomena in the presence of DTT, a reduction agent, which could cleave the disulfide bond between the micellar core and shell and consequently leading to the aggregation of hydrophobic core. Cytotoxicity study revealed that copolymers in this system have good biocompatibility and their self-assembled micelles showed a high drug loading efficiency for DOX, a hydrophobic drug model, and released DOX quantitatively in response to the intracellular level of reducing potential. Cellular uptake experiments demonstrated that the fluorescently labeled micelles could be successfully internalized into human liver carcinoma HepG2 cells, evidenced by confocal laser scanning microscopy. Above results indicate that the copolymers may have great potential in drug delivery to achieve improved cancer therapy.

Large-scale synthesis of α-amino acid-N-carboxyanhydrides

Hetero- and homopolymers prepared from α-amino acid-N-carboxyanhydrides (NCAs) monomers are widely useful products. The preparation of pure NCA monomers has been extensively studied in the past. Purification methods including repeated crystallizations, extraction, and flash column chromatography have been devised. However, these methods are not easily amendable to large-scale NCA preparations. This article describes the synthesis of numerous highly purified NCAs on a >100 g scale using a simple filtration step through diatomaceous earth (celite). The resulting NCAs provided polyethylene glycol (PEG)–amino acid triblock polymers devoid of low-molecular-weight by-products that were routinely observed when unfiltered batches of NCAs were used. Also disclosed is the preparation of NCAs at ambient temperature. Traditionally, NCA reactions using a phosgene source are heated. This study shows these reactions can be driven by the slight exotherm that forms upon reagent mixing. This eliminates the need for an external heating source, simplifying large-scale reactions.

COPOLYMERS FOR STABLE MICELLE FORMULATIONS

The present invention relates to the field of polymer chemistry and more particularly to multiblock copolymers and micelles comprising the same. Compositions herein are useful for drug-delivery applications.

BLOCK COPOLYMERS FOR STABLE MICELLES

The present invention relates to the field of polymer chemistry and more particularly to multiblock copolymers and micelles comprising the same. Compositions herein are useful for drug-delivery applications.

POLYMER MICELLES CONTAINING ANTHRACYLINES FOR THE TREATMENT OF CANCER

The present invention provides micelles having an anthracycline encapsulated therein, the micelles comprising a multiblock copolymer. The invention further provides methods of preparing and using said micelles, and compositions thereof.

HYBRID BLOCK COPOLYMER MICELLES WITH MIXED STEREOCHEMISTRY FOR ENCAPSULATION OF HYDROPHOBIC AGENTS

The present invention relates to the field of polymer chemistry and more particularly to multiblock copolymers and micelles comprising the same.

THE PREPARATION OF N-CARBOXYANHYDRIDES OF α-AMINO ACIDS USING BIS(TRICHLOROMETHYL)CARBONATE

A syntheis of the N-carboxyanhydrides (NCA's) of several α-amino acids using bis(trichloromethyl)carbonate, 1, is reported.The triphosgene is used to supply phosgene in situ in stoichiometric amounts; it is particularly effective for preparing NCA's of amino acids with long, aliphatic side chains.