(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Base Information

• Chemical Name: (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone
• CAS No.: 167280-64-0
• Molecular Formula: C₁₆H₁₇NO₆
• Molecular Weight: 319.314
• Mol file: 167280-64-0.mol

Synonyms:(-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Chemical Property of (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone

There total 4 articles about (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone 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: 82.0%

(+)-(5S)-1-Ethyl-5-<(benzyloxycarbonyl)amino>-3-oxo-2-(triphenylphosphoranylidene)hexanedioate (167280-63-9) → (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone (167280-64-0)

Guidance literature:

In tetrahydrofuran; for 48h; Heating;

DOI:10.1021/jo00110a026

Reference yield:

(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one (23632-66-8) → (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone (167280-64-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / (COCl)2, DMF / CH₂Cl₂ / 1.) 0 deg C, 2 h, 2.) 20 deg C, 16 h

2: 100 percent / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 20 deg C, 30 min

3: 77 percent / 1 N aq. NaOH / methanol / 4 h / 20 °C

4: 82 percent / tetrahydrofuran / 48 h / Heating

With sodium hydroxide; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00110a026

Reference yield:

(4S)-4-(Chloroformyl)methyl-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one (111197-44-5) → (-)-(4S,E)-Ethyl 3-<(benzyloxycarbonyl)amino>-5-<(ethoxycarbonyl)methylidene>-2-tetrahydrofuranone (167280-64-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) 20 deg C, 30 min

2: 77 percent / 1 N aq. NaOH / methanol / 4 h / 20 °C

3: 82 percent / tetrahydrofuran / 48 h / Heating

With sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo00110a026

upstream raw materials:

(+)-(5S)-1-Ethyl-5-<(benzyloxycarbonyl)amino>-3-oxo-2-(triphenylphosphoranylidene)hexanedioate

(4S)-3-benzyloxycarbonyl-4-carboxymethyl-1,3-oxazolidin-5-one

(4S)-4-(Chloroformyl)methyl-3-[(phenylmethoxy)carbonyl]oxazolidin-5-one

(+)-(4S)-3-(Benzyloxycarbonyl)-4-<3-(ethoxycarbonyl)-2-oxo-3-(triphenylphosphoranylidene)propyl>-1,3-oxazolidin-5-one

Downstream raw materials:

(+)-(5S)-Ethyl 5-<(benzyloxycarbonyl)amino>-5-carbamoyl>-3-oxopentanoate