(((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene

Base Information

• Chemical Name: (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene
• CAS No.: 1345817-45-9
• Molecular Formula: C₂₈H₃₆O₃
• Molecular Weight: 420.592

Synonyms:(((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene

Chemical Property of (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene

Chemical Property:

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Technology Process of (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene

There total 14 articles about (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene 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: 84.0%

(1R,2S)-2-((S,E)-3-((benzyloxy)methoxy)oct-1-en-1-yl)cyclopent-3-enol (1345817-44-8) + benzyl bromide (100-39-0) → (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene (1345817-45-9)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/ol202711k

Reference yield:

C19H34O2Si (1345817-39-1) → (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene (1345817-45-9)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridinium chlorochromate / dichloromethane / 20 °C

2: potassium hydroxide / dichloromethane; isopropyl alcohol / 16 h / 35 - 40 °C

3: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 30 °C

4: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 30 °C

5: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

6: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; potassium hydroxide; In tetrahydrofuran; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol202711k

Reference yield:

(1S,4R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl picolinate (1345817-36-8) → (((((S,E)-1-((1S,5R)-5-(benzyloxy)cyclopent-2-en-1-yl)oct-1-en-3-yl)oxy)methoxy)methyl)benzene (1345817-45-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: copper acetylacetonate / tetrahydrofuran; dichloromethane / 0.5 h / 0 °C

1.2: 2 h / 0 °C

2.1: potassium carbonate / methanol / 20 °C

3.1: n-butyllithium / hexane / 0.67 h / -70 °C

3.2: 3 h / -70 °C

4.1: pyridinium chlorochromate / dichloromethane / 20 °C

5.1: potassium hydroxide / dichloromethane; isopropyl alcohol / 16 h / 35 - 40 °C

6.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 30 °C

7.1: tetra-(n-butyl)ammonium iodide; N-ethyl-N,N-diisopropylamine / dichloromethane / 30 °C

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

9.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran / 20 °C

With copper acetylacetonate; n-butyllithium; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; pyridinium chlorochromate; potassium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol202711k

upstream raw materials:

(1S,4R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl picolinate

C₁₆H₃₀OSi₂

tert-butyl(((1R,2S)-2-ethynylcyclopent-3-en-1-yl)oxy)dimethylsilane

C₁₉H₃₄O₂Si

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