77877-19-1

Basic information

• Product Name: (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone
• Synonyms: (S)-3-Propionyl-4-isopropyl-2-oxazolidinone,99%e.e.;(S)-(+)-4-ISOPROPYL-3-PROPIONYL-2-OXAZOLIDINONE;(S)-4-ISOPROPYL-3-PROPIONYL-2-OXAZOLIDINONE;(S)-3-PROPIONYL-4-ISOPROPYL-2-OXAZOLIDINONE;N-PROPIONYL-(4S)-ISOPROPYL- 2-OXAZOLIDINONE;(S)-(+)-4-isopropyl-3-propimyl-2-oxazolidimone;(S)-(+)-4-ISOPRPYL-3-PROPIONYL-2-OXAZOLIDINONE;(S)-(+)-4-Isoprpyl-3-Propion
• CAS NO: 77877-19-1
• Molecular Formula: C₉H₁₅NO₃
• Molecular Weight: 185.22
• Product Categories: Oxazolidinone;chiral;Asymmetric Synthesis;Chiral Building Blocks;Glycidyl Compounds, etc. (Chiral);Synthetic Organic Chemistry;Peptide
• Mol File: 77877-19-1.mol

Chemical Properties

• Boiling Point: 102-106 °C0.75 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.094 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00162mmHg at 25°C
• Refractive Index: n20/D 1.465
• Storage Temp.: 2-8°C
• BRN: 3542849
• CAS DataBase Reference: (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone(77877-19-1)
• EPA Substance Registry System: (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone(77877-19-1)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 23-24/25-36-26
• WGK Germany: 3
• F: 3-10
• Hazardous Substances Data: 77877-19-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone is used as a reactant in the preparation of oxazolidinone derivatives, which serve as IL-6 signaling blockers. These blockers play a crucial role in modulating the immune response and have potential applications in the treatment of various inflammatory and autoimmune diseases.
Additionally, due to its unique chemical properties, (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone may also find applications in other industries, such as:
Used in Chemical Synthesis:
As a versatile building block, (S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone can be used in the synthesis of various complex organic molecules, contributing to the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
(S)-(+)-4-Isopropyl-3-propionyl-2-oxazolidinone's unique structure and properties make it a valuable tool for researchers in the field of organic chemistry and drug discovery. It can be employed in the design and synthesis of novel bioactive molecules, as well as in the study of various chemical reactions and mechanisms.

InChI:InChI=1/C9H15NO3/c1-4-8(11)10-7(6(2)3)5-13-9(10)12/h6-7H,4-5H2,1-3H3/t7-/m1/s1

Upstream product

• 79-03-8 propionyl chloride 
• 6216-65-5 N-benzyloxycarbonyl-L-valinol 
• 123-62-6 propionic acid anhydride 
• 95530-58-8 (R)-4-isopropyloxazolidin-2-one 
• 17016-83-0 (4S)-4-isopropyl-1,3-oxazolidin-2-one 
• 72-18-4 L-valine 
• 2026-48-4 (S)-valinol 
• 802294-64-0 propionic acid 
• 4122-52-5 1-(1H-imidazol-1-yl)propan-1-one 
• 80697-99-0 (S)-3-((R)-3-Benzyloxy-2-methyl-propionyl)-4-isopropyl-oxazolidin-2-one 

Downstream Products

• 116776-75-1 (S)-3-((2S,3S,4S)-3-Hydroxy-2,4-dimethyl-5-phenylsulfanyl-pentanoyl)-4-isopropyl-oxazolidin-2-one 
• 116805-52-8 (S)-3-((2S,3S,4R)-3-Hydroxy-2,4-dimethyl-5-phenylsulfanyl-pentanoyl)-4-isopropyl-oxazolidin-2-one 
• 155324-35-9 (2'R,3'S,4S)-3-(3'-hydroxy-2'-methyl-4'-oxo-4'-phenylbutyryl)-4-isopropyl-2-oxazolidinone 
• 155245-90-2 (2'R,3'R,4S)-3-(3'-hydroxy-2'-methyl-4'-oxo-4'-phenylbutyryl)-4-isopropyl-2-oxazolidinone 
• 155324-36-0 (2'S,3'S,4S)-3-(3'-hydroxy-2'-methyl-4'-oxo-4'-phenylbutyryl)-4-isopropyl-2-oxazolidinone 
• 104554-86-1 (+)-3-(5-Phenyl-2(R)-methyl-1-oxo-4(E)-pentenyl)-4(S)-isopropyl-1,3-oxazolidin-2-one 
• 1239600-18-0 (R)-3-((2R,3R)-3-hydroxy-2-methyl-4-methylenenonanoyl)-4-isopropyloxazolidin-2-one 
• 1419778-06-5 C₂₈H₃₁NO₇ 
• 1350547-30-6 C₁₈H₂₃NO₅ 
• 1259283-25-4 benzyl (2R,3R,4R)-3-hydroxy-5-[(R)-4-isopropyl-2-oxooxazolidin-3-yl]-4-methyl-5-oxo-1-phenylpentan-2-ylcarbamate 
• 1227632-99-6 (4R)-3-((2R,3S,6R)-7-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-3-hydroxy-2,6-dimethylheptanoyl)-4-isopropyl-1,3-oxazolan-2-one 
• 1132762-26-5 C₂₃H₂₉NO₄ 
• 160238-72-2 <3(2R,3S,5R,6S,7R),4R>-3-(7-benzoyloxy-5-benzyloxy-6-methoxy-3-(4-methoxybenzyl)oxy-2,8-dimethyl-1-oxononyl)-4-isopropyl-2-oxazolidinone 

Relevant articles and documents

Thermal proteome profiling efficiently identifies ribosome destabilizing oxazolidinones

Identifying the targets of bioactive small molecules is a challenging endeavor for which no general solution currently exists. Classical affinity purification experiments suffer from the need to functionalise a bioactive compound and link it to a solid support, which may interfere with target binding. A modern mass spectrometry-based proteomics technique that has partially circumvented this problem is thermal proteome profiling (TPP), which determines the effect of an unmodified small molecule on the thermal stability of the whole proteome simultaneously. Here, we use TPP to identify the mode-of-action of a newly-discovered autophagy inhibitor based on oxazolidinones often employed as chiral auxiliaries. Surprisingly, a significant portion of all ribosomal proteins were found to be destabilized by the inhibitor, highlighting the utility of this technology for determining a challenging mode-of-action.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

CONJUGATION LINKERS CONTAINING 2,3-DIAMINOSUCCINYL GROUP

Provided is a conjugate of a cytotoxic drug/molecule to a cell-binding molecule with a bis-linker (adual-linker) containing a 2, 3-diaminosuccinyl group. It also relates to preparation of the conjugate of a cytotoxic drug/molecule to a cell-binding molecule with the bis-linker, particularly when the drug having functional groups of amino, hydroxyl, diamino, amino-hydroxyl, dihydroxyl, carboxyl, hydrazine, aldehyde and thiol for conjugation with the bis-linker in a specific manner, as well as the therapeutic use of the conjugates.

A CONJUGATE OF A TUBULYSIN ANALOG WITH BRANCHED LINKERS

The present invention relates to the conjugation of a tubulysin analog compound to a cell-binding molecule with branched/side-chain linkers for having better delivery of the conjugate compound and targeted treatment of abnormal cells. It also relates to a branched-linkage method of conjugation of a tubulysin analog molecule to a cell-binding ligand, as well as methods of using the conjugate in targeted treatment of cancer, infection and autoimmune disease.

Synthesis of a diastereomer of the marine macrolide lytophilippine A

The synthesis of a diastereomer of lytophilippine A required 22 longest linear steps using known building blocks. Cross-metathesis/asymmetric aldol addition and regioselective esterification/ring-closing metathesis served as efficient combi tools for scaffold construction. Detailed NMR investigations in different solvent (systems) provide evidence for a deep-seated configurational misassignment of the molecule named lytophilippine A.

General and stereoselective aminoxylation of biradical titanium(iv) enolates with TEMPO: A detailed study on the effect of the chiral auxiliary

A comprehensive analysis of the influence of the chiral auxiliary on the α-aminoxylation of titanium(iv) enolates with TEMPO indicated that (S) 4-tert-butyl-1-oxazolidine-2-thione is the most appropriate scaffold to provide a single diastereomer in high yields for a variety of substrates, which converts such a radical reaction into a highly chemo- and stereoselective oxidation.

A method for synthesis of acylated oxazolidone

The invention discloses a method for synthesis of acylated oxazolidone. Synthesis method of the invention, comprising the following steps: in the non-protic organic solvent, the compound III and under the action of an acid, the compound I with compound II carries out amidation reaction, to obtain compound IV. The method of the invention can be conducted under mild conditions, high yield, high purity, and is suitable for industrial production requirements.

Structural Determination of (-)-SCH 64874 and Hirsutellomycin by Semisynthesis

The structure of a C2-symmetric epidithiodiketopiperazine alkaloid, SCH 64874, was determined by semisynthesis. The relative stereochemistry of the β-hydroxy carboxylic acid chain having three chiral centers was determined by comparison of the NMR data of the four possible diastereomeric β-hydroxy carboxylic acid fragments with those of SCH 64874. Condensation of the (-)-deacetylaranotin core with two enantiomeric β-hydroxy carboxylic acids revealed the relative stereochemistry of SCH 64874. The relative stereochemistry of the β-keto carboxylic acid chain of the analogous alkaloid hirsutellomycin was determined in a stepwise manner. The C4′-C6′ syn relationships were predicted by comparing the NMR data of the corresponding ester fragments with that of hirsutellomycin. The relative stereochemistry of the whole molecule, including the epimerizable C2′ stereocenter, was determined by introduction of four possible side chains into the bisdethiodi(methylthio)deacetylaranotin core. We found that the stereochemistry of C2′ converged with that of the thermodynamically stable form influenced by the core structure.

Stereocontrolled Syntheses of Seven-Membered Carbocycles by Tandem Allene Aziridination/[4+3] Reaction

A tandem allene aziridination/[4+3]/reduction sequence converts simple homoallenic sulfamates into densely functionalized aminated cycloheptenes, where the relative stereochemistry at five contiguous asymmetric centers can be controlled through the choice

Absolute configuration of lactams and oxazolidinones using kinetic resolution catalysts

A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An empirical mnemonic was developed for the assignment of the absolute configuration based on the fast-reacting catalyst.