ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate

Base Information

• Chemical Name: ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate
• CAS No.: 1454318-22-9
• Molecular Formula: C₂₆H₄₂O₆Si
• Molecular Weight: 478.701

Synonyms:ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate

Chemical Property of ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate

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Technology Process of ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate

There total 6 articles about ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate 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: 60.0%

1,5-dimethoxy-1,4-cyclohexadiene (37567-78-5) + ethyl (R)-5-(tert-butyldimethylsilyloxy)-6-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]hex-2-ynoate (1454318-23-0) → ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate (1454318-22-9)

Guidance literature:

With N,N-dimethyl-aniline; In neat (no solvent); at 200 ℃; for 48h; Inert atmosphere; Sealed tube;

DOI:10.1002/ejoc.201300053

Reference yield:

(+)-(5S)-hydroxy-(2E)-hexenal (93382-53-7) → ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate (1454318-22-9)

Guidance literature:

Multi-step reaction with 5 steps

1.1: AD-mix-α / tert-butyl alcohol; water / 0 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

2.2: tosylimidazole / 0.5 h / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

5.1: N,N-dimethyl-aniline / neat (no solvent) / 48 h / 200 °C / Inert atmosphere; Sealed tube

With 2,6-dimethylpyridine; n-butyllithium; AD-mix-α; sodium hydride; N,N-dimethyl-aniline; In tetrahydrofuran; hexane; dichloromethane; water; mineral oil; tert-butyl alcohol; 1.1: |Sharpless Dihydroxylation / 5.1: |Alder-Rickert Cycloaddition;

DOI:10.1002/ejoc.201300053

Reference yield:

(S)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propane-1,2-diol (1454318-25-2) → ethyl 2-{(R)-2-(tert-butyldimethylsilyloxy)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propyl}-4,6-dimethoxybenzoate (1454318-22-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere

1.2: tosylimidazole / 0.5 h / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / Inert atmosphere

2.2: 1 h / 0 °C / Inert atmosphere

3.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / 0 °C / Inert atmosphere

4.1: N,N-dimethyl-aniline / neat (no solvent) / 48 h / 200 °C / Inert atmosphere; Sealed tube

With 2,6-dimethylpyridine; n-butyllithium; sodium hydride; N,N-dimethyl-aniline; In tetrahydrofuran; hexane; dichloromethane; mineral oil; 4.1: |Alder-Rickert Cycloaddition;

DOI:10.1002/ejoc.201300053

upstream raw materials:

(S)-4-penten-2-ol

(+)-(5S)-hydroxy-(2E)-hexenal

(S)-3-[(2S,6S)-6-methyl-5,6-dihydro-2H-pyran-2-yl]propane-1,2-diol

(2S,6S)-2-methyl-6-[(S)-oxiran-2-ylmethyl]-3,6-dihydro-2H-pyran

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