(8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one

Base Information

• Chemical Name: (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one
• CAS No.: 1390618-96-8
• Molecular Formula: C₂₄H₃₈O₅
• Molecular Weight: 406.563
• Mol file: 1390618-96-8.mol

Synonyms:

Chemical Property of (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one

There total 10 articles about (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one 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:

C16H26O4 (1390618-98-0) → (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one (1390618-96-8)

Guidance literature:

Multi-step reaction with 6 steps

1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 25 °C

2: sodium hydride / tetrahydrofuran / 4 h / 28 °C

3: copper(l) iodide / tetrahydrofuran / 2 h / -30 °C

4: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 23 °C

5: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 2 h

6: 18-crown-6 ether; sodium hydride / 6 h / 28 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 18-crown-6 ether; sodium hydride; di(n-butyl)tin oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 6: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2012.05.094

Reference yield:

Ethyl oct-2-enoate (2351-90-8) → (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one (1390618-96-8)

Guidance literature:

Multi-step reaction with 9 steps

1: diisobutylaluminium hydride / dichloromethane / 2 h / 25 °C

2: titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate / dichloromethane / 6 h / -20 °C

3: titanium(IV) isopropylate / toluene / 2 h / Reflux

4: di(n-butyl)tin oxide; triethylamine / dichloromethane / 3 h / 25 °C

5: sodium hydride / tetrahydrofuran / 4 h / 28 °C

6: copper(l) iodide / tetrahydrofuran / 2 h / -30 °C

7: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 23 °C

8: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 2 h

9: 18-crown-6 ether; sodium hydride / 6 h / 28 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 18-crown-6 ether; L-(+)-diisopropyl tartrate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; toluene; 2: Sharpless epoxidation / 9: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2012.05.094

Reference yield:

C23H32O6S → (8S,9R,E)-9-(4-methoxybenzyloxy)-8-(methoxymethoxy)tetradec-4-en-3-one (1390618-96-8)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydride / tetrahydrofuran / 4 h / 28 °C

2: copper(l) iodide / tetrahydrofuran / 2 h / -30 °C

3: dmap; N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 23 °C

4: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 2 h

5: 18-crown-6 ether; sodium hydride / 6 h / 28 °C

With 2,6-dimethylpyridine; dmap; sodium periodate; copper(l) iodide; osmium(VIII) oxide; 18-crown-6 ether; sodium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 5: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.tetlet.2012.05.094

upstream raw materials:

C₁₆H₂₆O₄

(S)-2-((R)-1-((4-methoxybenzyl)oxy)hexyl)oxirane

(5S,6R)-6-((4-methoxybenzyl)oxy)undec-1-en-5-ol

1-methoxy-4-((((5S,6R)-5-(methoxymethoxy)undec-1-en-6-yl)oxy)methyl)benzene