(2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate

Base Information

• Chemical Name: (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate
• CAS No.: 1351987-32-0
• Molecular Formula: C₃₅H₅₀O₈
• Molecular Weight: 598.777
• Mol file: 1351987-32-0.mol

Synonyms:(2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate

Chemical Property of (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate

There total 41 articles about (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate 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: 71.0%

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene (900811-38-3) + (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate (1351987-26-2) → (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate (1351987-32-0)

Guidance literature:

(S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate; With lithium hydride; In N,N-dimethyl acetamide; at 60 ℃; for 1h;

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene; In N,N-dimethyl acetamide; at 60 ℃; for 48h;

DOI:10.1002/adsc.201200934

Reference yield: 68.0%

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene (900811-38-3) + (S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate (1351987-26-2) → (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate (1351987-32-0) + C34H48O8

Guidance literature:

With potassium hydrogencarbonate; In N,N-dimethyl acetamide; at 80 ℃; for 18h;

DOI:10.1021/acs.oprd.5b00396

Reference yield:

4-methoxy-3-(3-methoxypropoxy)benzaldehyde (172900-75-3) → (2R,S)(5S)-6-benzyl 1-ethyl 5-isopropyl-2-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutyl)-3-oxohexanedioate (1351987-32-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lithium diisopropyl amide / -40 °C / Inert atmosphere

2.1: camphor-10-sulfonic acid / toluene / Inert atmosphere

3.1: hydrogen; palladium on activated charcoal / methanol / Inert atmosphere

4.1: sodium hydroxide; water / ethanol / Reflux; Inert atmosphere

5.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

6.1: 20 °C / Inert atmosphere

7.1: Horse Liver Acetone Powder / N,N-dimethyl-formamide / 96 h / 25 °C / Resolution of racemate; Inert atmosphere

8.1: lithium aluminium tetrahydride / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

9.1: triethylamine / toluene / 1.5 h / 0 - 20 °C / Inert atmosphere

10.1: sodium iodide / acetonitrile / 12 h / Inert atmosphere; Reflux

11.1: lithium hydride / N,N-dimethyl acetamide / 1 h / 60 °C / Inert atmosphere

11.2: 48 h / 60 °C / Inert atmosphere

With lithium aluminium tetrahydride; oxalyl dichloride; Horse Liver Acetone Powder; palladium on activated charcoal; camphor-10-sulfonic acid; water; hydrogen; lithium hydride; triethylamine; N,N-dimethyl-formamide; sodium iodide; sodium hydroxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: |Aldol Addition;

DOI:10.1021/acs.oprd.5b00396

upstream raw materials:

(S)-3-(benzyloxycarbonyl)-4-methylpentanoic acid

(R)--4-(2-(iodomethyl)--3--methylbutyl)--1--methoxy-2--(3--methoxypropoxy)benzene

(S)-1-benzyl-6-ethyl-2-isopropyl-4-oxohexanedioate

ethyl 2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoate

Refernces

• 1、 Cini, Elena,Banfi, Luca,Barreca, Giuseppe,Carcone, Luca,Malpezzi, Luciana,Manetti, Fabrizio,Marras, Giovanni,Rasparini, Marcello,Riva, Renata,Roseblade, Stephen,Russo, Adele,Taddei, Maurizio,Vitale, Romina,Zanotti-Gerosa, Antonio. "Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5-C6 Disconnection and CO2H-NH2 Equivalence". . p. 270 - 283. Retrieved 2016/03/04.