Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester

Base Information

• Chemical Name: Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester
• CAS No.: 85864-17-1
• Molecular Formula: C₁₉H₂₅NO₄
• Molecular Weight: 331.412
• Mol file: 85864-17-1.mol

Synonyms:Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester

Chemical Property of Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester

There total 8 articles about Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl 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:

(2E,4E)-methylhexa-2,4-dienoate (689-89-4) → Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester (85864-17-1)

Guidance literature:

Multi-step reaction with 8 steps

1: 1) LDA, HMPA / 1) THF, hexane, -78 deg C, 1h, 2) 0 deg C, then room temp., 4 h

2: 92 percent / LDA, HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

3: 68 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

4: 86 percent / KH / tetrahydrofuran / 0.5 h / 0 °C

5: 5percent HCl / acetone / 0.08 h / Ambient temperature

6: 85 percent / Jones reagent / acetone / 0.25 h / 0 °C

7: 1) pyridine, ethyl chloroformate, 2) conc. NH₃ / 1) THF, 0 deg C, 0.5 h, 2) H₂O

8: 1) cesium carbonate, 2) pyridine / 1)THF, room temp., 12 h, 2) 15 min

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium hydroxide; lithium aluminium tetrahydride; jones reagent; chloroformic acid ethyl ester; potassium hydride; caesium carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; acetone;

DOI:10.1021/jo00169a009

Reference yield:

(2E,4E)-2-(3,3-Dimethoxy-propyl)-hexa-2,4-dienoic acid methyl ester (85864-11-5) → Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester (85864-17-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / LDA, HMPA / tetrahydrofuran; hexane / 3 h / -78 °C

2: 68 percent / LiAlH₄ / diethyl ether / 0.5 h / 0 °C

3: 86 percent / KH / tetrahydrofuran / 0.5 h / 0 °C

4: 5percent HCl / acetone / 0.08 h / Ambient temperature

5: 85 percent / Jones reagent / acetone / 0.25 h / 0 °C

6: 1) pyridine, ethyl chloroformate, 2) conc. NH₃ / 1) THF, 0 deg C, 0.5 h, 2) H₂O

7: 1) cesium carbonate, 2) pyridine / 1)THF, room temp., 12 h, 2) 15 min

With pyridine; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; ammonium hydroxide; lithium aluminium tetrahydride; jones reagent; chloroformic acid ethyl ester; potassium hydride; caesium carbonate; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; acetone;

DOI:10.1021/jo00169a009

Reference yield:

(5E)-4-benzyloxymethyl-5,7-octadienal (85864-14-8) → Acetic acid ((E)-4-benzyloxymethyl-octa-5,7-dienoylamino)-methyl ester (85864-17-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / Jones reagent / acetone / 0.25 h / 0 °C

2: 1) pyridine, ethyl chloroformate, 2) conc. NH₃ / 1) THF, 0 deg C, 0.5 h, 2) H₂O

3: 1) cesium carbonate, 2) pyridine / 1)THF, room temp., 12 h, 2) 15 min

With pyridine; ammonium hydroxide; jones reagent; chloroformic acid ethyl ester; caesium carbonate; In acetone;

DOI:10.1021/jo00169a009

upstream raw materials:

formaldehyd

acetic anhydride

(E)-4-Benzyloxymethyl-octa-5,7-dienoic acid amide

(2E,4E)-methylhexa-2,4-dienoate

Downstream raw materials:

(1S,9aR)-1-Benzyloxymethyl-1,2,3,6,7,9a-hexahydro-quinolizin-4-one