3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: 3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one
• CAS No.: 300592-63-6
• Molecular Formula: C₂₅H₃₁NO₃S
• Molecular Weight: 425.592
• Mol file: 300592-63-6.mol

Synonyms:3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one

Chemical Property of 3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one

There total 1 articles about 3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-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: 84.0%

(4S)-3-((2S)-2-bromo-3-methylbutanoyl)-4-benzyl-1,3-oxazolidin-2-one (113543-35-4) + 4-t-butylbenzenethiol (2396-68-1) → 3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one (300592-63-6)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ja992543i

Reference yield: 92.0%

3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one (300592-63-6) → (2R)-2-(4-tert-butylphenylthio)-3-methylbutan-1-ol (300592-73-8)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; water; at 0 ℃; for 3h;

DOI:10.1021/ja992543i

Reference yield:

3-[(2R)-2-(4-tert-butylphenylthio)-3-methylbutanoyl]-(4S)-4-benzyl-1,3-oxazolidin-2-one (300592-63-6) → 2-(4-tert-butyl-phenylsulfanyl)-3-methyl-butyraldehyde

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / LiBH₄ / tetrahydrofuran; H₂O / 3 h / 0 °C

2: oxalyl chloride; DMSO; DIPEA / CH₂Cl₂ / -78 - -50 °C

With lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; 2: Swern oxidation;

DOI:10.1021/ja992543i

upstream raw materials:

(4S)-3-((2S)-2-bromo-3-methylbutanoyl)-4-benzyl-1,3-oxazolidin-2-one

4-t-butylbenzenethiol

Downstream raw materials:

(2R)-2-(4-tert-butylphenylthio)-3-methylbutan-1-ol

(2S,3R)-3-(4-tert-butylphenylthio)-4-methylpentan-2-ol

(2R,3R)-3-(4-tert-butylphenylthio)-4-methylpentan-2-ol