5-Hexenoic acid, (1R,3R)-3-[(4-methoxyphenyl)methoxy]-1-propyl-4-pentenyl ester

Base Information

• Chemical Name: 5-Hexenoic acid, (1R,3R)-3-[(4-methoxyphenyl)methoxy]-1-propyl-4-pentenyl ester
• CAS No.: 721923-23-5
• Molecular Formula: C22H32O4
• Molecular Weight: 360.494
• Mol file: 721923-23-5.mol

Synonyms:

Chemical Property of 5-Hexenoic acid, (1R,3R)-3-[(4-methoxyphenyl)methoxy]-1-propyl-4-pentenyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-Hexenoic acid, (1R,3R)-3-[(4-methoxyphenyl)methoxy]-1-propyl-4-pentenyl ester

There total 19 articles about 5-Hexenoic acid, (1R,3R)-3-[(4-methoxyphenyl)methoxy]-1-propyl-4-pentenyl 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: 86.0%

5-hexenoic acid (1577-22-6) + (4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-ol (721923-22-4) → (4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-yl hex-5-enoate (721923-23-5)

Guidance literature:

(4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-ol; With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 ℃; for 0.166667h; Inert atmosphere;

5-hexenoic acid; In dichloromethane; at 0 - 20 ℃; for 15h; Inert atmosphere;

Reference yield:

O1,O2-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose (4613-68-7,14260-67-4,22248-90-4,74996-06-8) → (4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-yl hex-5-enoate (721923-23-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 82 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 0 °C

2: 92 percent / H₂ / Pd/C / 3 h / 20 °C / 750.08 Torr

3: aq. AcOH; concd. H₂SO₄ / H₂O / 6 h / Heating

4: 76 percent / n-BuLi / tetrahydrofuran / 12 h / 0 - 20 °C

5: 94 percent / NaH / dimethylformamide / 1 h / 0 °C

6: 82 percent / 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 4 h / 0 - 20 °C

With dmap; n-butyllithium; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; water; N,N-dimethyl-formamide; 4: Wittig reaction / 6: Yamaguchi reaction;

DOI:10.1016/j.tetlet.2004.04.040

Reference yield:

3-deoxy-1,2-O-isopropylidene-D-glucose (4005-46-3,4494-96-6,22248-87-9,142941-40-0) → (4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-yl hex-5-enoate (721923-23-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 95 percent / NaIO₄ / CH₂Cl₂ / 0.5 h / 20 °C

2: 82 percent / n-BuLi / tetrahydrofuran / 3 h / -78 - 0 °C

3: 92 percent / H₂ / Pd/C / 3 h / 20 °C / 750.08 Torr

4: aq. AcOH; concd. H₂SO₄ / H₂O / 6 h / Heating

5: 76 percent / n-BuLi / tetrahydrofuran / 12 h / 0 - 20 °C

6: 94 percent / NaH / dimethylformamide / 1 h / 0 °C

7: 82 percent / 2,4,6-trichlorobenzoyl chloride; DMAP / tetrahydrofuran / 4 h / 0 - 20 °C

With dmap; sodium periodate; n-butyllithium; sulfuric acid; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 5: Wittig reaction / 7: Yamaguchi reaction;

DOI:10.1016/j.tetlet.2004.04.040

upstream raw materials:

5-hexenoic acid

(4R,6R)-6-(4-methoxybenzyloxy)oct-7-en-4-ol

O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose

3-deoxy-1,2-O-isopropylidene-D-glucose