(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

Base Information

• Chemical Name: (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid
• CAS No.: 949023-16-9
• Molecular Formula: C₂₄H₂₁NO₅
• Molecular Weight: 403.434
• DSSTox Substance ID: DTXSID40453238
• Mol file: 949023-16-9.mol

Synonyms:949023-16-9;(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid;(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-5-oxazolidinecarboxylic acid;(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid;SCHEMBL7071105;DTXSID40453238;RDVJYGYJBUIIOE-ZOAFEQKISA-N;AMY21997;MFCD11617943;AKOS015904212;AC-22280;DS-18606;CS-0150397;F13037;(4S,5R)-2-(4-methoxyphenyl)-N-benzoyl-4-phenyl-oxazolidine-5-carboxylic acid;(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylicacid

Chemical Property of (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Boiling Point: 642.269 °C at 760 mmHg
• PKA: 2.85±0.60(Predicted)
• Flash Point: 342.232 °C
• PSA: 76.07000
• Density: 1.291 g/cm³
• LogP: 3.99880
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 403.14197277
• Heavy Atom Count: 30
• Complexity: 590

Purity/Quality:

99% ^*data from raw suppliers

(4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C2N(C(C(O2)C(=O)O)C3=CC=CC=C3)C(=O)C4=CC=CC=C4
• Isomeric SMILES: COC1=CC=C(C=C1)C2N([C@H]([C@@H](O2)C(=O)O)C3=CC=CC=C3)C(=O)C4=CC=CC=C4
• Uses: Modification of (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic Acid which has similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel.

Technology Process of (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid

There total 35 articles about (4S,5R)-3-Benzoyl-2-(4-methoxyphenyl)-4-phenyloxazolidine-5-carboxylic acid 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: 97.0%

(2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (157826-10-3,949023-16-9) → (2S,4S,5R)-3-Benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (202390-86-1,949023-16-9)

Guidance literature:

(2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid; With p-Anisaldehyde dimethyl acetal; (R)-10-camphorsulfonic acid; In toluene; at 20 - 130 ℃; Large scale;

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 0.333333h; Large scale;

Reference yield: 95.0%

[(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-methanone (162189-18-6) → (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (157826-10-3,949023-16-9)

Guidance literature:

With lithium hydroxide; dihydrogen peroxide; In tetrahydrofuran; water; at 0 ℃; for 0.416667h;

DOI:10.1039/c39940002591

Reference yield: 86.0%

Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate (157826-09-0) → (2R,4S,5R)-3-benzoyl-2-(4-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylic acid (157826-10-3,949023-16-9)

Guidance literature:

With lithium hydroxide; water; In tetrahydrofuran; methanol; at 20 ℃; for 0.5h;

DOI:10.1002/(sici)1521-3765(19990104)5:1<121::aid-chem121>3.3.co;2-f

upstream raw materials:

[(2R,4S,5R)-3-Benzoyl-2-(4-methoxy-phenyl)-4-phenyl-oxazolidin-5-yl]-((1R,5S,7S)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-methanone

Methyl (2R,4S,5R)-3-benzoyl-2-(p-methoxyphenyl)-4-phenyl-1,3-oxazolidine-5-carboxylate

1-methoxy-4-(methoxymethyl)benzene

methyl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropanoate

Refernces

• 1、 -. "Synthetic method of paclitaxel side chain". Paragraph 0010-0012. . Retrieved 2020/10/21.
• 2、 -. "Preparation method of side chain of paclitaxel". Paragraph 0040; 0041; 0043; 0044; 0045; 0046. . Retrieved 2018/11/22.