(S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate

Base Information

• Chemical Name: (S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate
• CAS No.: 847406-37-5
• Molecular Formula: C19H25NO5
• Molecular Weight: 347.411
• Hs Code.: 2934999090
• Mol file: 847406-37-5.mol

Synonyms:(S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate;(betaS,4R)-beta-Methyl-gama,2-dioxo-4-(phenylmethyl)-3-oxazolidinebutanoic acid tert-butyl ester

Chemical Property of (S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate

Chemical Property:

• PSA: 72.91000
• Density: 1.172
• LogP: 2.88230

Purity/Quality:

99% BY HPLC ^*data from raw suppliers

(S)-tert-Butyl4-((S)-4-benzyl-2-oxooxazolidin-3-yl)-3-methyl-4-oxobutanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate

There total 4 articles about (S)-tert-butyl 4-((S)-4-benzyl-2-oxooxazolidin-3-yl) -3-Methyl-4-oxobutanoate 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: 82.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → (4R)-N-[(2S)-3-(tert-butoxycarbonyl)-2-methylpropanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one (847406-37-5)

Guidance literature:

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 3h;

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

DOI:10.1055/s-0033-1340872

Reference yield: 31.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (3R)-3-propionyl-4-benzyloxazolidin-2-one (101711-78-8,131685-53-5) → tert-butyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-methyl-4-oxobutanoate + (4R)-N-[(2S)-3-(tert-butoxycarbonyl)-2-methylpropanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one (847406-37-5)

Guidance literature:

(3R)-3-propionyl-4-benzyloxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; Inert atmosphere;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; for 3h; optical yield given as %de; Inert atmosphere;

DOI:10.1002/anie.200802223

Reference yield:

tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate (865704-46-7) + methyl iodide (74-88-4) → tert-butyl (3R)-4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-3-methyl-4-oxobutanoate + (4R)-N-[(2S)-3-(tert-butoxycarbonyl)-2-methylpropanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one (847406-37-5)

Guidance literature:

tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 - -50 ℃; Title compound not separated from byproducts;

DOI:10.1055/s-2005-865362

upstream raw materials:

tert-butyl 4-[(4R)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]-4-oxobutanoate

methyl iodide

bromoacetic acid tert-butyl ester

(3R)-3-propionyl-4-benzyloxazolidin-2-one

Downstream raw materials:

C₃₃H₄₃N₃O₆

Refernces

• 1、 Kawamura, Shuhei,Unno, Yuka,Asai, Akira,Arisawa, Mitsuhiro,Shuto, Satoshi. "Design and synthesis of the stabilized analogs of belactosin A with the unnatural cis-cyclopropane structure". supporting information. p. 6615 - 6622. Retrieved 2013/09/24.
• 2、 Rodriguez-Escrich, Carles,Urpi, Felix,Vilarrasa, Jaume. "Stereocontrolled total synthesis of amphidinolide X via a silicon-tethered metathesis reaction". scheme or table. p. 5191 - 5194. Retrieved 2009/06/06.