191090-32-1

Basic information

• Product Name: (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE
• Synonyms: (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE;(R)-4-Isopropyl-5,5-diphenyl-2-oxazolidinone,99%e.e.;(4R)-5,5-diphenyl-4-propan-2-yl-1,3-oxazolidin-2-one
• CAS NO: 191090-32-1
• Molecular Formula: C₁₈H₁₉NO₂
• Molecular Weight: 281.35
• Product Categories: Intermediates of Sertraline;Asymmetric Synthesis;Chiral Auxiliaries;Oxazolidinone Derivatives
• Mol File: 191090-32-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 252-255 °C(lit.)
• Boiling Point: 475.7 °C at 760 mmHg
• Flash Point: 241.5 °C
• Appearance: /
• Density: 1.12 g/cm³
• Vapor Pressure: 3.25E-09mmHg at 25°C
• Refractive Index: 1.562
• PKA: 11.74±0.60(Predicted)
• CAS DataBase Reference: (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(191090-32-1)
• EPA Substance Registry System: (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE(191090-32-1)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 191090-32-1(Hazardous Substances Data)

Usage

General Description

(R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE is a chemical compound used in organic synthesis as a chiral auxiliary. It is a white crystalline solid with a molecular formula of C20H23NO2 and a molecular weight of 309.40 g/mol. (R)-(+)-4-ISOPROPYL-5,5-DIPHENYL-2-OXAZOLIDINONE is commonly used as a resolving agent for a wide range of acids, esters, and acids, as well as a building block for various pharmaceuticals and agricultural chemicals. Its chiral nature makes it useful in the asymmetric synthesis of a variety of complex organic molecules, making it an important tool in the field of organic chemistry.

InChI:InChI=1/C18H19NO2/c1-13(2)16-18(21-17(20)19-16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-13,16H,1-2H3,(H,19,20)/t16-/m1/s1

Upstream product

• 58561-04-9 N-tert-butoxycarbonyl-L-valine methyl ester 
• 67-56-1 methanol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 443761-68-0 (R)-3-[(2R,3S,4S)-3-[(tert-butyldimethylsilanyl)oxy]-5-hydroxy-2,4-dimethylpentanoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 649755-75-9 (R)-3-[(2R,3S,4S)-2,4-dimethyl-3,5-bis(triethylsilanyloxy)pentanoyl]-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 
• 443761-79-3 (R)-3-[(2R,3R)-3-hydroxy-2,4-dimethylpent-4-enoyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 223906-53-4 (4R)-N-Propionyl-5,5-diphenyl-4-isopropyloxazolidin-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 
• 7146-15-8 D-Valine methyl ester hydrochloride 
• 100-51-6 benzyl alcohol 
• 223906-36-3 (2R)-N-Boc-2-amino-1,1-diphenyl-3-methylbutanol 
• 640-68-6 D-Val-OH 
• 106391-85-9 (R)-methyl 2-((tert-butoxycarbonyl)amino)-3-methylbutanoate 

Downstream Products

• 357271-57-9 (R)-4-(1-methylethyl)-3-(1-oxo-5-phthalimidohexanoyl)-5,5-diphenyloxazolidin-2-one 
• 637337-51-0 C₂₉H₂₆N₂O₅ 
• 1267597-50-1 (R)-4-isopropyl-3-((S)-2-methylpent-4-enoyl)-5,5-diphenyloxazolidin-2-one 
• 916831-21-5 (R)-3-(2-Trifluoromethylphenyl)pyrrolidine 
• 1108203-24-2 (R,E)-3-(4-(tert-butyldimethylsilyloxy)but-2-enoyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 637337-63-4 (R)-3-[(2S,3S)-2-({[(benzyloxy)carbonyl]amino}methyl)-3-methyl-1-oxopentyl]-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 671233-56-0 (R)-4-isopropyl-3-((S)-2-{[(methoxycarbonyl)amino]methyl}-4-(methylsulfanyl)-1-oxobutyl)-4-isopropyl-5,5-diphenyloxazolidin-2-one 
• 842141-71-3 (R)-4-Isopropyl-3-((R)-2-methyl-hept-6-enoyl)-5,5-diphenyl-oxazolidin-2-one 
• 637337-17-8 (4R)-3-[(2S)-6-azido-2-({[(benzyloxy)carbonyl]amino}methyl)-1-oxohexyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-60-1 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-6-bromo-1-oxohexyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-59-8 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-5-bromo-1-oxopentyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-58-7 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-bromo-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-64-5 (4R)-3-[(2S)-2-({[(benzyloxy)carbonyl]amino}methyl)-4-(methylsulfanyl)-1-oxobutyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 
• 637337-09-8 (4R)-[(2R,3S)-2-({[(tert-butoxy)carbonyl]amino}methyl)-3-hydroxy-1-oxopropyl]-4-(1-methylethyl)-5,5-diphenyloxazolidin-2-one 

Relevant articles and documents

Synthesis and application of N-3,5-dinitrobenzoyl and C3 symmetric diastereomeric chiral stationary phases

Three diastereomeric chiral compounds, namely, (R,R)-(+)-2-amino-1,2-diphenylethanol, (1S,2R)-(+)-2-amino-1,2-diphenylethanol, and (1R,2R)-(+)-1,2-diphenylethylenediamine were used as starting materials for preparing three N-3,5-dinitrobenzoyl derivative

Synthesis of new C3 symmetric amino acid- and aminoalcohol-containing chiral stationary phases and application to HPLC enantioseparations

We recently reported a new C3-symmetric (R)-phenylglycinol N-1,3,5-benzenetricarboxylic acid-derived chiral high-performance liquid chromatography (HPLC) stationary phase (CSP 1) that demonstrated better results as compared to a previously described N-3,5-dintrobenzoyl (DNB) (R)-phenylglycinol-derived CSP. Over a decade ago, (S)-leucinol, (R)-phenylglycine, and (S)-leucine derivatives were used as the starting materials of 3,5-DNB-based Pirkle-type CSPs for chiral separation. In this study, three new C3-symmetric CSPs (CSP 2, 3, and 4) were prepared by combining the ideas and results mentioned above. Here we describe the synthetic procedures and applications of the new C3-symmetric CSPs (CSP 2–CSP 4).

A practical building block for the synthesis of discodermolide

A new highly diastereoselective and practical route to the lactone 6a which is used as a key building block for the total synthesis of the microtubule-stabilizing anticancer agent discodermolide is reported. This exploits the chiral auxiliary (4R)-4-isopr