(R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one
• CAS No.: 1239664-46-0
• Molecular Formula: C₂₁H₃₃NO₄Si
• Molecular Weight: 391.583
• Mol file: 1239664-46-0.mol

Synonyms:(R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one

Chemical Property of (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one

There total 4 articles about (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one (907593-86-6) → (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one (1239664-46-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 5.5h; Inert atmosphere;

DOI:10.1021/ol402820d

Reference yield:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one (1239664-46-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

2.2: 0.5 h / 0 °C / Inert atmosphere

2.3: 3 h / 0 °C / Inert atmosphere

3.1: hydrogen; palladium 10% on activated carbon / ethanol; dichloromethane / 23 h / 20 °C / Inert atmosphere

4.1: triethylamine; dmap / dichloromethane / 5.5 h / 0 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; palladium 10% on activated carbon; hydrogen; titanium tetrachloride; triethylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/ol402820d

Reference yield:

(R)-3-(1-butyryl)-4-benzyloxazolidine-2-one (111292-87-6,112459-79-7,143097-11-4) → (R)-4-benzyl-3-[(S)-2-(tert-butyldimethylsilyloxymethyl)butanoyl]oxazolidin-2-one (1239664-46-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: titanium tetrachloride / dichloromethane / 0.17 h / 0 °C / Inert atmosphere

1.2: 0.5 h / 0 °C / Inert atmosphere

1.3: 3 h / 0 °C / Inert atmosphere

2.1: hydrogen; palladium 10% on activated carbon / ethanol; dichloromethane / 23 h / 20 °C / Inert atmosphere

3.1: triethylamine; dmap / dichloromethane / 5.5 h / 0 - 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; hydrogen; titanium tetrachloride; triethylamine; In ethanol; dichloromethane;

DOI:10.1021/ol402820d

upstream raw materials:

tert-butyldimethylsilyl chloride

(R)-4-benzyl-3-[(S)-2-(hydroxymethyl)butanoyl]oxazolidin-2-one

(R)-4-(phenylmethyl)-2-oxazolidinone

(R)-3-(1-butyryl)-4-benzyloxazolidine-2-one

Downstream raw materials:

(R)-2-((tert-butyldimethylsilyloxy)methyl)butan-1-ol

(R)-4-(phenylmethyl)-2-oxazolidinone

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

(4R)-4-benzyl-3-((2R,3S,4R)-3-hydroxy-2,4-dimethylhexanoyl)oxazolidin-2-one