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

Base Information

• Chemical Name: (S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate
• CAS No.: 851518-35-9
• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.449
• Mol file: 851518-35-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate 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: 93.0%

bromoacetic acid tert-butyl ester (5292-43-3) + (4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one (155399-10-3) → (S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate (851518-35-9)

Guidance literature:

(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h;

bromoacetic acid tert-butyl ester; In tetrahydrofuran; at -78 - -48 ℃;

DOI:10.1016/j.bmcl.2009.09.089

Reference yield:

(R)-4-(phenylmethyl)-2-oxazolidinone (40217-17-2,90719-32-7,120574-96-1,102029-44-7) → (S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate (851518-35-9)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexanes;

Reference yield:

pent-4-enoyl chloride (39716-58-0) → (S)-tert-butyl 3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoate (851518-35-9)

Guidance literature:

Multi-step reaction with 2 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

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran; hexanes;

upstream raw materials:

bromoacetic acid tert-butyl ester

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

pent-4-enoyl chloride

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

Downstream raw materials:

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

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

2-((3R,11S,E)-5,12-dioxo-3-phenyl-1-oxa-4-azacyclododec-8-en-11-yl)acetic acid

tert-butyl 2-((3R,11S,E)-5,12-dioxo-3-phenyl-1-oxa-4-azacyclododec-8-en-11-yl)acetate