(2E,4E,6R,7R)-ethyl7-hydroxy-4,6- dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate

Base Information

• Chemical Name: (2E,4E,6R,7R)-ethyl7-hydroxy-4,6- dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate
• CAS No.: 934246-96-5
• Molecular Formula: C17H21NO5
• Molecular Weight: 319.357
• Mol file: 934246-96-5.mol

Synonyms:Ethyl (2E,4E,6R,7R)-7-hydroxy-4,6-dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate;(2E,4E,6R,7R)-ethyl7-hydroxy-4,6- diMethyl-7-(4-nitrophenyl)hepta-2,4-dienoate

Chemical Property of (2E,4E,6R,7R)-ethyl7-hydroxy-4,6- dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate

Chemical Property:

• PSA: 92.35000
• LogP: 3.85310

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (2E,4E,6R,7R)-ethyl7-hydroxy-4,6- dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate

There total 4 articles about (2E,4E,6R,7R)-ethyl7-hydroxy-4,6- dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate 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: 96.0%

(E)-(4R,5R)-5-hydroxy-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-enal (934246-95-4) + diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) → ethyl (2E,4E)-(6R,7R)-7-hydroxy-4,6-dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate (934246-96-5)

Guidance literature:

diethoxyphosphoryl-acetic acid ethyl ester; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.333333h;

(E)-(4R,5R)-5-hydroxy-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-enal; In tetrahydrofuran; at 20 ℃; for 0.5h;

DOI:10.1002/adsc.200606106

Reference yield:

4-nitrobenzaldehdye (555-16-8) → ethyl (2E,4E)-(6R,7R)-7-hydroxy-4,6-dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate (934246-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: L-proline / dimethylformamide / 5 h / 0 °C

1.2: CH₂Cl₂; toluene / 3 h / Heating

2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

2.2: 96 percent / tetrahydrofuran / 0.5 h / 20 °C

With sodium hydride; L-proline; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/adsc.200606106

Reference yield:

(E)-(4R,5R)-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-ene-1,5-diol (934246-94-3) → ethyl (2E,4E)-(6R,7R)-7-hydroxy-4,6-dimethyl-7-(4-nitrophenyl)hepta-2,4-dienoate (934246-96-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 663 mg / γ-MnO2 / CH2Cl2 / 1 h / 20 °C

2.1: NaH / tetrahydrofuran / 0.33 h / 20 °C

2.2: 96 percent / tetrahydrofuran / 0.5 h / 20 °C

With manganese(IV) oxide; sodium hydride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/adsc.200606106

upstream raw materials:

(E)-(4R,5R)-5-hydroxy-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-enal

diethoxyphosphoryl-acetic acid ethyl ester

(E)-(4R,5R)-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-ene-1,5-diol

methyl (E)-(4R,5R)-5-hydroxy-2,4-dimethyl-5-(4-nitrophenyl)-pent-2-enoate

Downstream raw materials:

ethyl (2E,4E)-(6R,7R)-7-(4-aminophenyl)-7-hydroxy-4,6-dimethylhepta-2,4-dienoate