(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

Base Information

• Chemical Name: (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid
• CAS No.: 851518-40-6
• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.342
• Mol file: 851518-40-6.mol

Synonyms:(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

Chemical Property of (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

There total 3 articles about (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid 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: 87.0%

(S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate (851518-35-9) → (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid (851518-40-6)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja048170p

Reference yield:

(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one (155399-10-3) → (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid (851518-40-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / LDA / tetrahydrofuran / 2.33 h / -78 °C

2: 87 percent / TFA; Et₃SiH / CH₂Cl₂ / 2 h / 20 °C

With triethylsilane; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja048170p

Reference yield:

pent-4-enoyl chloride (39716-58-0) → (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid (851518-40-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.17 h / -78 °C

1.2: 1.5 h / -78 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 4 h / -78 - -48 °C

3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

With n-butyllithium; sodium hexamethyldisilazane; trifluoroacetic acid; In tetrahydrofuran; hexanes; dichloromethane;

upstream raw materials:

(S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate

(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

pent-4-enoyl chloride

Downstream raw materials:

(S)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enoic acid

(S)-2-allyl-N₄-(4-chlorobenzyl)-N₁-((R)-2-hydroxy-2-phenylethyl)succinamide

N-(4-chlorobenzyl)-2-((2R,6S,E)-5,12-dioxo-2-phenyl-1-oxa-4-azacyclododec-8-en-6-yl)acetamide

(R)-2-((S)-2-(2-(4-chlorobenzylamino)-2-oxoethyl)pent-4-enamido)-1-phenylethyl pent-4-enoate