223906-53-4

Basic information

• Product Name: 2-Oxazolidinone, 4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyl-, (4R)-
• CAS NO: 223906-53-4
• Molecular Formula: C21H23NO3
• Molecular Weight: 337.419
• Mol File: 223906-53-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-Oxazolidinone, 4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyl-, (4R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Oxazolidinone, 4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyl-, (4R)-(223906-53-4)
• EPA Substance Registry System: 2-Oxazolidinone, 4-(1-methylethyl)-3-(1-oxopropyl)-5,5-diphenyl-, (4R)-(223906-53-4)

Safety Data

• Hazardous Substances Data: 223906-53-4(Hazardous Substances Data)

Upstream product

• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 223906-36-3 (2R)-N-Boc-2-amino-1,1-diphenyl-3-methylbutanol 
• 79-03-8 propionyl chloride 
• 191090-32-1 (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one 
• 106391-85-9 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate 
• 7146-15-8 D-Valine methyl ester hydrochloride 
• 640-68-6 D-Val-OH 

Downstream Products

• 1070774-68-3 (R)-N-[(S)-2,4-dimethyl-pent-4-enoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 1359872-26-6 (4R)-4-isopropyl-3-[(2S)-2-methylpent-4-ynoyl]-5,5-diphenyl-1,3-oxazolidin-2-one 
• 1267597-50-1 (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one 
• 1601495-46-8 C₂₅H₂₉NO₃ 
• 1601495-66-2 C₂₅H₂₇NO₃ 
• 443761-68-0 (R)-3-[(2R,3S,4S)-3-[(tert-butyldimethylsilanyl)oxy]-5-hydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 443761-70-4 (R)-3-[(2R,3S,4S)-3,5-bis[(tert-butyldimethylsilyl)oxy]-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 443761-69-1 (R)-3-[(2R,3S,4S)-3,5-dihydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 191090-32-1 (R)-4-(1-methylethyl)-5,5-diphenyl-1,3-oxazolidin-2-one 
• 649755-76-0 (R)-3-[(2R,3S,4S)-5-hydroxy-2,4-dimethyl-3-(triethylsilanyloxy)pentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 1003279-57-9 (R)-3-((S,E)-2,4-dimethylhex-4-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 649755-85-1 (R)-3-[(Z)-(2R,3S,4S,5S,6S)-3-hydroxy-2,4,6-trimethyl-5-triethylsilanyloxy-deca-7,9-dienoyl]-4-isopropyl-5,5-diphenyl-oxazolidin-2-one 
• 443761-79-3 (R)-3-[(2R,3R)-3-hydroxy-2,4-dimethylpent-4-enoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 

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 peptide-embedded trifluoromethyl ketone catalyst for enantioselective epoxidation

The development of peptide-based oxidation catalysts that use a transiently generated dioxirane as the chemically active species is reported. The active catalyst is a chiral trifluoromethyl ketone (Tfk) with a pendant carboxylic acid that can be readily incorporated into a peptide. These peptides were capable of epoxidizing alkenes in high yield (up to 89%) and enantiomeric ratios (er) ranging from 69.0:31.0 to 91.0:9.0, depending on the alkene substitution pattern.

Asymmetric alkylations using SuperQuat auxiliaries - An investigation into the synthesis and stability of enolates derived from 5,5-disubstituted oxazolidin-2-ones

Studies on the alkylation of enolates derived from a range of N-acyl-5,5-dimethyloxazolidin-2-ones and N-acyl-5,5-diphenyloxazolidin-2-ones reveal that high yields and high diastereoselectivities are best obtained when homochiral 4-isopropyl-5,5-dimethyloxazolidin-2-one is employed as a chiral auxiliary.