(1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate

Base Information

• Chemical Name: (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate
• CAS No.: 1190042-34-2
• Molecular Formula: C₂₂H₃₂O₄
• Molecular Weight: 360.494
• Mol file: 1190042-34-2.mol

Synonyms:(1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate

Chemical Property of (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate

There total 8 articles about (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate 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: 81.0%

(5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoic acid (1190042-35-3) + (4R)-hept-1-en-ol (3521-91-3,85520-72-5,111321-98-3,67760-84-3) → (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate (1190042-34-2)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 3h;

DOI:10.2174/157017811794697502

Reference yield:

[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-methanol (251571-56-9) → (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate (1190042-34-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 6 h

2.1: diisobutylaluminium hydride / dichloromethane; toluene / 6 h / -78 °C

3.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h

3.2: 0.5 h / -78 - 20 °C

4.1: toluene / 2 h

5.1: platinum(IV) oxide; hydrogen; sodium hydrogencarbonate / ethyl acetate / 12 h

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

7.2: 0.5 h / -78 - 20 °C

8.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

8.2: 1 h / 0 °C / Inert atmosphere

9.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 20 °C

10.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C

With 1H-imidazole; dmap; platinum(IV) oxide; oxalyl dichloride; lithium hydroxide monohydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; 3.1: |Swern Oxidation / 4.1: |Wittig-Horner Reaction / 7.1: |Swern Oxidation / 8.2: |Wittig Olefination;

DOI:10.2174/157017811794697502

Reference yield:

(3S)-4-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-3-[(4-methoxybenzyl)oxy]butan-1-ol (221677-48-1) → (1R)-1-propyl-3-butenyl (5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoate (1190042-34-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h

1.2: 0.5 h / -78 - 20 °C

2.1: toluene / 2 h

3.1: platinum(IV) oxide; hydrogen; sodium hydrogencarbonate / ethyl acetate / 12 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 0 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

5.2: 0.5 h / -78 - 20 °C

6.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C / Inert atmosphere

6.2: 1 h / 0 °C / Inert atmosphere

7.1: lithium hydroxide monohydrate; water / tetrahydrofuran; methanol / 4 h / 20 °C

8.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 3 h / 20 °C

With dmap; platinum(IV) oxide; oxalyl dichloride; lithium hydroxide monohydrate; potassium tert-butylate; tetrabutyl ammonium fluoride; water; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene; 1.1: |Swern Oxidation / 2.1: |Wittig-Horner Reaction / 5.1: |Swern Oxidation / 6.2: |Wittig Olefination;

DOI:10.2174/157017811794697502

upstream raw materials:

(5S)-5-[(4-methoxybenzyl)oxy-]6-heptenoic acid

(4R)-hept-1-en-ol

(3S)-4-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-3-[(4-methoxybenzyl)oxy]butan-1-ol

[(S)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-methanol

Downstream raw materials:

C₂₀H₂₈O₄

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