(2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

Base Information

• Chemical Name: (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide
• CAS No.: 896104-74-8
• Molecular Formula: C₂₀H₃₁NO₄
• Molecular Weight: 349.47

Synonyms:(2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

Chemical Property of (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

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Technology Process of (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide

There total 2 articles about (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide 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%

(E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid (896104-51-1) + N,0-dimethylhydroxylamine (1117-97-1) → (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide (896104-74-8)

Guidance literature:

With methanesulfonyl chloride; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo0604585

Reference yield: 30.0%

(E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid (896104-51-1) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → (2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide (896104-74-8)

Guidance literature:

With pyridine; carbon tetrabromide; triphenylphosphine; at 20 ℃; for 0.5h;

DOI:10.1021/jo048385h

Reference yield: 82.0%

(2S,3S,4E)-N-methoxy-2-{3-[(4-methoxybenzyl)oxy]propyl}-N,3-dimethylhex-4-enamide (896104-74-8) + vinyl magnesium bromide (1826-67-1) → (E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one (896104-52-2)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jo0604585

upstream raw materials:

(E)-(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-hex-4-enoic acid

N,O-dimethylhydroxylamine*hydrochloride

N,0-dimethylhydroxylamine

Downstream raw materials:

(E)-(4S,5S)-4-[3-(4-Methoxy-benzyloxy)-propyl]-5-methyl-octa-1,6-dien-3-one

(4S,5S)-5-[3-(4-Methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-2-enone

(2S,3S)-2-[3-(4-Methoxy-benzyloxy)-propyl]-3-methyl-cyclopentanone

Trifluoro-methanesulfonic acid (4S,5S)-5-[3-(4-methoxy-benzyloxy)-propyl]-4-methyl-cyclopent-1-enyl ester

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