N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

Base Information

Chemical Name:N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide
CAS No.:787632-46-6
Molecular Formula:C₃₅H₅₃NO₆
Molecular Weight:583.809
Hs Code.:

Synonyms:N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

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Chemical Property of N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

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Technology Process of N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

There total 7 articles about N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide 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: 80.0%

: 1120-36-1
1-tetradecene

: 787632-41-1
N-[(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-pent-4-enyl]-acetamide

: 787632-46-6
N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 8h;
DOI:10.1016/j.tetlet.2004.08.030

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 787632-46-6
N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / NaH / dimethylformamide / 0 °C

2.1: 60 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3.1: tetrahydrofuran / -50 - 20 °C

4.1: MsCl; Et₃N / tetrahydrofuran / 0 - 20 °C

4.2: aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

4.3: potassium carbonate / tetrahydrofuran / 8 h / 60 °C / pH 9.5

5.1: 80 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 8 h / 40 °C

With sodium hydride; diisobutylaluminium hydride; methanesulfonyl chloride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.08.030

Reference yield:

: 787632-40-0
N-[(1R,2S)-2-(4-Methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-3-oxo-propyl]-acetamide

: 787632-46-6
N-[(E)-(1R,2S,3S)-3-Hydroxy-2-(4-methoxy-benzyloxy)-1-(4-methoxy-phenoxymethyl)-heptadec-4-enyl]-acetamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: tetrahydrofuran / -50 - 20 °C

2.1: MsCl; Et₃N / tetrahydrofuran / 0 - 20 °C

2.2: aq. HCl / tetrahydrofuran / 0.5 h / 20 °C

2.3: potassium carbonate / tetrahydrofuran / 8 h / 60 °C / pH 9.5

3.1: 80 percent / second generation Grubbs' catalyst / CH₂Cl₂ / 8 h / 40 °C

With methanesulfonyl chloride; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetlet.2004.08.030