6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester

Base Information

• Chemical Name: 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester
• CAS No.: 871838-06-1
• Molecular Formula: C₄₀H₅₁N₃O₃
• Molecular Weight: 621.863
• Mol file: 871838-06-1.mol

Synonyms:6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester

Chemical Property of 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester

There total 17 articles about 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester 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: 57.0%

1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone (871838-08-3) + 5-methyl-3-oxo-hexanoic acid ethyl ester (34036-16-3) → 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester (871838-06-1)

Guidance literature:

5-methyl-3-oxo-hexanoic acid ethyl ester; With ammonium acetate; In toluene; for 1h; Heating;

1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone; With ytterbium(III) triflate; In toluene; for 48h; Heating;

DOI:10.1021/ol0521228

Reference yield:

4-benzyloxybutanal (5470-84-8) → 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester (871838-06-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 54 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

2.1: 79 percent / CrO₃; H₂SO₄ / acetone; H₂O / 0.67 h / 0 °C

3.1: ammonium acetate / toluene / 1 h / Heating

3.2: 65 percent / ytterbium(III) triflate / toluene / 48 h / Heating

4.1: 82 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

5.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

6.1: 89 percent / tetrahydrofuran / -78 - 0 °C

7.1: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

8.1: ammonium acetate / toluene / 1 h / Heating

8.2: 78 percent / ytterbium(III) triflate / toluene / 48 h / Heating

9.1: 78 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

10.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

11.1: 53 percent / tetrahydrofuran / -78 - 0 °C

12.1: 67 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

13.1: ammonium acetate / toluene / 1 h / Heating

13.2: 57 percent / ytterbium(III) triflate / toluene / 48 h / Heating

With chromium(VI) oxide; ammonium acetate; manganese(IV) oxide; oxalyl dichloride; sulfuric acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 2.1: Jones oxidation / 3.2: Bohlmann-Rahtz heteroannulation / 5.1: Swern oxidation / 8.2: Bohlmann-Rahtz heteroannulation / 10.1: Swern oxidation / 13.2: Bohlmann-Rahtz heteroannulation;

DOI:10.1021/ol0521228

Reference yield:

4-benzyloxy-butan-1-ol (4541-14-4) → 6''-(3-benzyloxy-propyl)-6,2',2''-triisobutyl-[2,3';6',3'']terpyridine-5-carboxylic acid ethyl ester (871838-06-1)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 89 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

2.1: 54 percent / tetrahydrofuran / 2.5 h / -78 - 0 °C

3.1: 79 percent / CrO₃; H₂SO₄ / acetone; H₂O / 0.67 h / 0 °C

4.1: ammonium acetate / toluene / 1 h / Heating

4.2: 65 percent / ytterbium(III) triflate / toluene / 48 h / Heating

5.1: 82 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

6.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

7.1: 89 percent / tetrahydrofuran / -78 - 0 °C

8.1: 89 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

9.1: ammonium acetate / toluene / 1 h / Heating

9.2: 78 percent / ytterbium(III) triflate / toluene / 48 h / Heating

10.1: 78 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 °C

11.1: 90 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.42 h / -78 - 0 °C

12.1: 53 percent / tetrahydrofuran / -78 - 0 °C

13.1: 67 percent / MnO₂ / CH₂Cl₂ / 3 h / 20 °C

14.1: ammonium acetate / toluene / 1 h / Heating

14.2: 57 percent / ytterbium(III) triflate / toluene / 48 h / Heating

With chromium(VI) oxide; ammonium acetate; manganese(IV) oxide; oxalyl dichloride; sulfuric acid; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; water; acetone; toluene; 1.1: Swern oxidation / 3.1: Jones oxidation / 4.2: Bohlmann-Rahtz heteroannulation / 6.1: Swern oxidation / 9.2: Bohlmann-Rahtz heteroannulation / 11.1: Swern oxidation / 14.2: Bohlmann-Rahtz heteroannulation;

DOI:10.1021/ol0521228

upstream raw materials:

1-[6'-(3-benzyloxy-propyl)-6,2'-diisobutyl-[2,3']bipyridinyl-5-yl]-propynone

5-methyl-3-oxo-hexanoic acid ethyl ester

6-(3-benzyloxy-propyl)-2-isobutyl-pyridine-3-carbaldehyde

[6-(3-benzyloxy-propyl)-2-isobutyl-pyridin-3-yl]-methanol