(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

Base Information

• Chemical Name: (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one
• CAS No.: 951172-59-1
• Molecular Formula: C₂₁H₂₁NO₄
• Molecular Weight: 351.402
• Mol file: 951172-59-1.mol

Synonyms:(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

Chemical Property of (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

There total 5 articles about (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)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: 91.0%

allyl iodid (556-56-9) + (S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester (171860-41-6) → (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one (951172-59-1)

Guidance literature:

(S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.25h;

allyl iodid; In tetrahydrofuran; at -78 - 20 ℃; for 21h; Further stages.;

DOI:10.1021/jo071074x

Reference yield: 80.0%

(S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester (171860-41-6) + allyl bromide (106-95-6) → (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one (951172-59-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 3h; stereoselective reaction; Inert atmosphere;

DOI:10.1002/chir.22474

Reference yield:

N-Cbz-Ala (1142-20-7) → (2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one (951172-59-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: thionyl chloride / tetrahydrofuran / 0.5 h / 0 °C

1.2: 3 h / 0 °C

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.33 h / -78 °C

2.2: 15 h / -78 - 20 °C

With thionyl chloride; lithium hexamethyldisilazane; In tetrahydrofuran;

upstream raw materials:

allyl iodid

(S,S)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester

N-Cbz-Ala

benzyl chloroformate

Downstream raw materials:

(2S,4S)-3-benzyloxycarbonyl-4-methyl-4-(2-oxoethyl)-2-phenyloxazolidin-5-one