(4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone
• CAS No.: 197721-33-8
• Molecular Formula: C₂₀H₂₅NO₅
• Molecular Weight: 359.422
• Mol file: 197721-33-8.mol

Synonyms:(4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone

Chemical Property of (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone

There total 6 articles about (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone 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:

2-(pent-4-en-1-yloxy)acetic acid (160239-22-5) → (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone (197721-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / diethyl ether / 1.08 h / -78 - 0 °C

2: 1.) n-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min

3: Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, from -40 deg C to -30 deg C, 2.) CH₂Cl₂, a.) -78 deg C, 1.5 h, b) from -78 deg C to 0 deg C, 30 min

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; triethylamine; In diethyl ether;

DOI:10.1021/ja990421k

Reference yield:

acrolein (107-02-8,25068-14-8) + (S)-3-<1-oxo-2-(pent-4-enyl-1-oxy)>-4-benzyl-2-oxazolidinone (197721-30-5) → (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone (197721-33-8)

Guidance literature:

With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 ℃; Yield given;

DOI:10.1021/jo9716688

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → (4S)-3-<(2S,3R)-1-oxo-2-(pent-4-enyl-1-oxy)-3-hydroxy-4-pentenyl>-4-benzyl-2-oxazolidinone (197721-33-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaH / 1.) THF, a) 0 deg C, 15 min, b) from 0 deg C to 25 deg C, 15 min, 2.) THF, 25 deg C, 3 h

2: Et₃N / diethyl ether / 1.08 h / -78 - 0 °C

3: 1.) n-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, ether, a) -78 deg C, 15 min, b) from -78 deg C to 0 deg C, 30 min

4: Bu₂BOTf, Et₃N / 1.) CH₂Cl₂, from -40 deg C to -30 deg C, 2.) CH₂Cl₂, a.) -78 deg C, 1.5 h, b) from -78 deg C to 0 deg C, 30 min

With n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; sodium hydride; triethylamine; In diethyl ether;

DOI:10.1021/ja990421k

upstream raw materials:

acrolein

(S)-3-<1-oxo-2-(pent-4-enyl-1-oxy)>-4-benzyl-2-oxazolidinone

n-Pent-4-enyl alcohol

(S)-4-Benzyl-2-oxazolidinone