202874-73-5

Usage

Uses

Used in Pharmaceutical Industry:
(4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one is used as a chiral building block for the development of new pharmaceutical compounds. Its specific stereochemistry and functional groups enable the creation of novel drugs with improved efficacy and selectivity.
Used in Organic Synthesis:
In the field of organic synthesis, (4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one serves as a versatile intermediate for the synthesis of various complex molecules. Its unique structure allows for further functionalization and modification, leading to the development of new compounds with diverse applications.
Used in Research and Development:
(4S)-3-((2R)-4-(tert-butoxy)-2-methyl-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one is used as a research compound to study its properties and potential applications. Its unique stereochemistry and functional groups make it an interesting target for scientists to explore its reactivity, stability, and interactions with other molecules, which could lead to the discovery of new reactions and applications in various industries.

Upstream product

• 5292-43-3 bromoacetic acid tert-butyl ester 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 

Downstream Products

• 185836-75-3 (R)-3-tert-butyloxycarbonyl-2-methylpropanoic acid 

Relevant academic research and scientific papers

Total synthesis of the proposed structure for itralamide b

A stereocontrolled total synthesis of the cyclodepsipeptide, itralamide B, has been achieved. Both R- and S-stereoisomers of the side chain were attached to the macrocyclic ring, however, the synthesized structure appears to be different from that of the

Discovery of the First Potent, Selective, and Orally Bioavailable Signal Peptide Peptidase-Like 2a (SPPL2a) Inhibitor Displaying Pronounced Immunomodulatory Effects in Vivo

Signal peptide peptidase-like 2a (SPPL2a) is an aspartic intramembrane protease which has recently been shown to play an important role in the development and function of antigen presenting cells such as B lymphocytes and dendritic cells. In this paper, we describe the discovery of the first selective and orally active SPPL2a inhibitor (S)-2-cyclopropyl-N1-((S)-5,11-dioxo-10,11-dihydro-1H,3H,5H-spiro[benzo[d]pyrazolo[1,2-a][1,2]diazepine-2,1′-cyclopropan]-10-yl)-N4-(5-fluoro-2-methylpyridin-3-yl)succinamide 40 (SPL-707). This compound shows adequate selectivity against the closely related enzymes γ-secretase and SPP and a good pharmacokinetic profile in mouse and rat. Compound 40 significantly inhibited processing of the SPPL2a substrate CD74/p8 fragment in rodents at doses ≤10 mg/kg b.i.d. po. Oral dosing of 40 for 11 days at ≥10 mg/kg b.i.d. recapitulated the phenotype seen in Sppl2a knockout (ko) and ENU mutant mice (reduced number of specific B cells and myeloid dendritic cells). Thus, we believe that SPPL2a represents an interesting and druggable pharmacological target, potentially providing a novel approach for the treatment of autoimmune diseases by targeting B cells and dendritic cells.

A general method for the synthesis of enantiomerically pure β- substituted, β-amino acids through α-substituted succinic acid derivatives

A general procedure for the synthesis of enantiopure β-substituted, β- amino acids is presented. Alkylation of the sodium enolates derived from chiral N-acyloxazolidinone imides 2 (R = Me, i-Pr, t-Bu, Ph, Bn) with tert- butyl bromoacetate afforded the 2-substituted succinate derivatives 3 in good yields (82-89%) and with high selectivity (≥ 93;7). Following hydrolysis, Curtius rearrangement of the resulting carboxylic acid provided the enantiopure benzyloxycarbonyl (Cbz)-protected β-amino esters 6 in good yields (74-79%).