1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde

Base Information

• Chemical Name: 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde
• CAS No.: 856688-70-5
• Molecular Formula: C₃₁H₄₄N₂O₄Si
• Molecular Weight: 536.787

Synonyms:1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde

Chemical Property of 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde

Chemical Property:

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Technology Process of 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde

There total 9 articles about 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde 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:

(1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl){[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl]-5-phenylpentyl}-1H-pyrazol-4-yl)methanol (856688-62-5) → 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde (856688-70-5)

Guidance literature:

With pyridine-SO₃ complex; triethylamine; In dimethyl sulfoxide; ethyl acetate; at 20 ℃; for 1h;

Reference yield:

3,5-dimethoxy-4-methylbenzaldehyde (1011-27-4) → 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde (856688-70-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine; chloro-trimethyl-silane; magnesium chloride / ethyl acetate / 20 °C

1.2: 0.08 h

2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

3.1: lithium borohydride / tetrahydrofuran; water / 3 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 0.25 h / 0 - 20 °C

5.1: sodium iodide / acetone / 3 h / 90 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 20 °C

8.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; lithium borohydride; chloro-trimethyl-silane; sulfur trioxide pyridine complex; potassium carbonate; triethylamine; sodium iodide; magnesium chloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsmedchemlett.7b00383

Reference yield:

(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one (161725-13-9) → 1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazole-4-carbaldehyde (856688-70-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine; chloro-trimethyl-silane; magnesium chloride / ethyl acetate / 20 °C

1.2: 0.08 h

2.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 0 °C

3.1: lithium borohydride / tetrahydrofuran; water / 3 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine / tetrahydrofuran / 0.25 h / 0 - 20 °C

5.1: sodium iodide / acetone / 3 h / 90 °C

6.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 60 °C

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.25 h / 20 °C

8.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; lithium borohydride; chloro-trimethyl-silane; sulfur trioxide pyridine complex; potassium carbonate; triethylamine; sodium iodide; magnesium chloride; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acsmedchemlett.7b00383

upstream raw materials:

(1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl){[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl]-5-phenylpentyl}-1H-pyrazol-4-yl)methanol

3,5-dimethoxy-4-methylbenzaldehyde

(4S)-4-benzyl-3-(5-phenylpentanoyl)-1,3-oxazolidin-2-one

(4S)-4-benzyl-3-{(2R)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentanoyl}-1,3-oxazolidin-2-one

Downstream raw materials:

ethyl (2E)-3-(1-{(2S)-2-[(S)-(3,5-dimethoxy-4-methylphenyl)(hydroxy)methyl]-5-phenylpentyl}-1H-pyrazol-4-yl)acrylate

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