(4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone
• CAS No.: 77943-39-6
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 29349990
• European Community (EC) Number: 853-687-1
• UNII: 05339K0T1Y
• Nikkaji Number: J411.516C
• Wikidata: Q27236062
• Mol file: 77943-39-6.mol

Synonyms:4-methyl-5-phenyl-1,3-oxazolidin-2-one;4-methyl-5-phenyl-1,3-oxazolidin-2-one, (cis-(+-))-isomer;MePh-2-oxazolidinone

Chemical Property of (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 1.79E-06mmHg at 25°C
• Melting Point: 121-123 °C(lit.)
• Refractive Index: 1.526
• Boiling Point: 395.8 °C at 760 mmHg
• PKA: 12.35±0.60(Predicted)
• Flash Point: 193.2 °C
• PSA: 38.33000
• Density: 1.132 g/cm³
• LogP: 2.18480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 199

Purity/Quality:

97% ^*data from raw suppliers

(4R,5S)-4-Methyl-5-phenyloxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(OC(=O)N1)C2=CC=CC=C2
• Isomeric SMILES: C[C@@H]1[C@@H](OC(=O)N1)C2=CC=CC=C2
• Uses: (4R,5S)-4-Methyl-5-phenyloxazolidinone is used as effective chiral auxiliary for conjugate addition asymmetric synthesis of (-)-aplysillamide B. Evan′s chiral auxiliary (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone reacts with carboxylic acids to produce corresponding acyl derivatives in the presence of a diisopropylcarbodiimide reagent. It can also employed in the preparation of N-sulfinyloxazolidinone reagent (chiral sulfinyl transfer reagent), which reacts with nucleophiles such as Grignard reagents, enolates, and metalated amides to produce the chiral sulfoxides, sulfinate esters, and sulfonamides.

Technology Process of (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

There total 116 articles about (4R,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + mephenoxalone (70-07-5) → 4-methyl-5-phenyloxazolidin-2-one (77943-39-6)

Guidance literature:

With hydrogenchloride; AlMe₃; In tetrahydrofuran; hexane; dichloromethane;

Reference yield: 100.0%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + (4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one (779353-80-9) → (E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoic acid methoxy-methyl-amide (541511-47-1) + 4-methyl-5-phenyloxazolidin-2-one (77943-39-6)

Guidance literature:

N,O-dimethylhydroxylamine*hydrochloride; With trimethylaluminum; In tetrahydrofuran; toluene; at 0 - 20 ℃;

(4R,5S)-3-((E)-(2R,3R)-3-Hydroxy-2,4-dimethyl-hept-4-enoyl)-4-methyl-5-phenyl-oxazolidin-2-one; In tetrahydrofuran; toluene; at 0 ℃; for 1h;

DOI:10.1016/j.tet.2004.06.125

Reference yield: 99.0%

carbon monoxide (201230-82-2) + (1S,2R)-(+)-norphedrine (37577-28-9,58550-13-3,757124-50-8) → 4-methyl-5-phenyloxazolidin-2-one (77943-39-6)

Guidance literature:

With copper diacetate; air; palladium diacetate; In toluene; for 2h; under 760 Torr; Heating;

DOI:10.1021/jo060612n

upstream raw materials:

(2RS,3SR)-3-hydroxy-2-methyl-3-phenyl-propionic acid hydrazide

norepinephrine

Diethyl carbonate

sodium carbonate

Downstream raw materials:

norephedrine

(4R,5S)-4-methyl-5-phenyl-3-<(R)-p-tolylsulfinyl>-2-isoxazolidinone

(4R,5S)-4-methyl-5-phenyl-3-<(S)-p-tolylsulfinyl>-2-isoxazolidinone

(4R,5S)-3-(1-oxo-2-bromoethyl)-4-methyl-5-phenyl-2-oxazolidinone

Refernces

Nonracemic α-Fluoro Aldehydes: Asymmetric Synthesis of 4-Deoxy-4-fluoro-D-arabinopyranose

10.1021/jo9714829

The research focuses on the enantioselective synthesis of epimerizable R-fluoro aldehydes and their application in the synthesis of 4-deoxy-4-fluoro-D-arabinopyranose. Key chemicals involved in this research include 3-(benzyloxy)-1-propanol, which was oxidized to an acid and then converted to an acid chloride. The acid chloride reacted with the lithium salt of (4R,5S)-(+)-4-methyl-5-phenyl-2-oxazolidinone to form an intermediate. Electrophilic fluorination using N-fluorobenzenesulfonimide (NFSi) yielded a crucial R-fluoro carboximide. Reduction with LiBH4 produced a 2-fluorohydrin, which was subsequently oxidized using the Dess-Martin periodinane reagent to form the desired R-fluoro aldehydes. These aldehydes were then used in a Horner-Wadsworth-Emmons reaction and a Sharpless asymmetric dihydroxylation to ultimately synthesize the target 4-deoxy-4-fluoro-D-arabinopyranose. The study highlights the importance of fluorine in enhancing biological and pharmacological activity, and the challenges and successes in synthesizing and utilizing chiral R-fluoro aldehydes as building blocks.

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