(R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate

Base Information

• Chemical Name: (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate
• CAS No.: 1430811-70-3
• Molecular Formula: C₂₂H₃₆N₃O₄P
• Molecular Weight: 437.519

Synonyms:(R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate

Chemical Property of (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate

Chemical Property:

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Technology Process of (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate

There total 7 articles about (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate 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: 72.0%

(E)-dimethyl 2-[(R)-2-(4-octylphenethyl)oxiran-2-yl]vinylphosphonate (1430811-67-8) → (S,E)-dimethyl 3-azido-3-(hydroxymethyl)-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-69-0) + (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-70-3)

Guidance literature:

With sodium azide; ammonium chloride; In ethanol; at 100 ℃; for 0.333333h; regioselective reaction; Inert atmosphere; Microwave irradiation;

DOI:10.1016/j.bmc.2013.02.042

Reference yield:

4-octylbenzaldehyde (49763-66-8) → (S,E)-dimethyl 3-azido-3-(hydroxymethyl)-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-69-0) + (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-70-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran / 3 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

3.1: sodium hydroxide / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

3.2: 3 h / 60 °C / Inert atmosphere

4.1: hydrogenchloride; water / methanol / 1 h / 20 °C / Inert atmosphere

5.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / Inert atmosphere

5.2: 2 h / 20 °C / Inert atmosphere

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

6.2: 1 h / 0 °C / Inert atmosphere

7.1: ammonium chloride; sodium azide / ethanol / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation

With titanium(IV) isopropylate; hydrogenchloride; n-butyllithium; sodium azide; water; sodium hydride; D-(-)-diisopropyl tartrate; ammonium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; mineral oil; 1.2: |Wittig Olefination / 3.2: |Suzuki Coupling / 5.1: |Sharpless Asymmetric Epoxidation / 5.2: |Dess-Martin Oxidation / 6.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.bmc.2013.02.042

Reference yield:

C24H39B → (S,E)-dimethyl 3-azido-3-(hydroxymethyl)-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-69-0) + (R,E)-dimethyl 3-(azidomethyl)-3-hydroxy-5-(4-octylphenyl)pent-1-enylphosphonate (1430811-70-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydroxide / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

1.2: 3 h / 60 °C / Inert atmosphere

2.1: hydrogenchloride; water / methanol / 1 h / 20 °C / Inert atmosphere

3.1: titanium(IV) isopropylate; D-(-)-diisopropyl tartrate / Inert atmosphere

3.2: 2 h / 20 °C / Inert atmosphere

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

4.2: 1 h / 0 °C / Inert atmosphere

5.1: ammonium chloride; sodium azide / ethanol / 0.33 h / 100 °C / Inert atmosphere; Microwave irradiation

With titanium(IV) isopropylate; hydrogenchloride; sodium azide; water; sodium hydride; D-(-)-diisopropyl tartrate; ammonium chloride; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; water; mineral oil; 1.2: |Suzuki Coupling / 3.1: |Sharpless Asymmetric Epoxidation / 3.2: |Dess-Martin Oxidation / 4.2: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.bmc.2013.02.042

upstream raw materials:

1-octyl-4-vinylbenzene

2-methylene-4-(4'-octylphenyl)butan-1-ol

(S)-2-(4-octylphenethyl)oxirane-2-carboxaldehyde

(E)-dimethyl 2-[(R)-2-(4-octylphenethyl)oxiran-2-yl]vinylphosphonate

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