(2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one

Base Information

• Chemical Name: (2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one
• CAS No.: 113806-30-7
• Molecular Formula: C₂₃H₁₉NO₃
• Molecular Weight: 357.409
• DSSTox Substance ID: DTXSID601190072
• Nikkaji Number: J857.200C
• Mol file: 113806-30-7.mol

Synonyms:(2R)-2alpha-Phenyl-3-benzoyl-4beta-benzyloxazolidin-5-one;3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one;ZQIYMSGCSHJWRW-RBBKRZOGSA-N;(2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one;DTXSID601190072;AJ-797/40757649;(2R,4S)-3-Benzoyl-2-phenyl-4-(phenylmethyl)-5-oxazolidinone;113806-30-7

Chemical Property of (2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one

Chemical Property:

• XLogP3: 4.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 357.13649347
• Heavy Atom Count: 27
• Complexity: 516

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2C(=O)OC(N2C(=O)C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H]2C(=O)O[C@@H](N2C(=O)C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of (2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one

There total 1 articles about (2R,4S)-3-benzoyl-4-benzyl-2-phenyl-1,3-oxazolidin-5-one 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:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + benzaldehyde (100-52-7) + benzoyl chloride (98-88-4) → (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7)

Guidance literature:

With sodium hydroxide; Multistep reaction; 1.) 1,2-DCE, reflux 2.) 1,2-DCE, -20 -> 4 deg C;

DOI:10.1016/S0040-4039(98)02125-X

Reference yield: 93.0%

allyl bromide (106-95-6) + (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7) → (2R,4R)-4-Allyl-3-benzoyl-4-benzyl-2-phenyl-oxazolidin-5-one (219788-52-0)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1016/S0040-4039(03)00882-7

Reference yield: 87.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one (113806-30-7) → (2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate (258854-42-1)

Guidance literature:

(2R,4S)-3-benzoyl-4-benzyl-2-phenyloxazolidin-5-one; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.116667h;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo991306v

upstream raw materials:

L-phenylalanine

benzaldehyde

benzoyl chloride

Downstream raw materials:

Ethyl (2'R,4'S)-(+)-4-(3'-benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)-3-oxo-2-(triphenylphosphoranylidene)butanoate

((2'R,4'S)-(+)-3'-Benzoyl-4'-benzyl-5'-oxo-2'-phenyloxazolidin-4'-yl)acetic acid

(2R,4R)-4-Allyl-3-benzoyl-4-benzyl-2-phenyl-oxazolidin-5-one

(2R,4S)-tert-butyl 3-benzoyl-4-benzyl-5-oxo-2-phenyl-1,3-oxazolidin-4-yl ethanoate