(1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis

Base Information

• Chemical Name: (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis
• CAS No.: 948995-45-7
• Molecular Formula: C₃₉H₅₄O₉
• Molecular Weight: 666.852

Synonyms:(1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis

Chemical Property of (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis

There total 4 articles about (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acis 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: 86.0%

[2-(trimethylsilyl)ethoxy]methyl (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylate (948995-44-6) → (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylic acis (948995-45-7)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; pyridine; at 0 ℃; for 72h;

DOI:10.1021/jo0708442

Reference yield:

(1S,2R,3Z,5S,6R,7S,10R,13R)-5-ethynyl-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylic acid (854490-37-2) → (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylic acis (948995-45-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 92 percent / Et₃N / tetrahydrofuran / 1.5 h / 0 °C

2.1: Bu₃SnH / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 0.33 h

2.2: 73 percent / I₂ / CH₂Cl₂ / 0.08 h / 0 °C

3.1: 91 percent / AsPh₃; CuI / Pd₂(dba)3 / dimethylformamide / 1 h / 60 °C

4.1: 86 percent / HF*pyridine complex / tetrahydrofuran; pyridine / 72 h / 0 °C

With copper(l) iodide; triphenyl-arsane; tri-n-butyl-tin hydride; pyridine hydrogenfluoride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 3.1: Stille coupling;

DOI:10.1021/jo0708442

Reference yield:

[2-(trimethylsilyl)ethoxy]methyl (1S,2R,5S,6R,7S,10R,13R)-5-ethynyl-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylate (948995-42-4) → (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylic acis (948995-45-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₃SnH / Pd(PPh₃)2Cl₂ / tetrahydrofuran / 0.33 h

1.2: 73 percent / I₂ / CH₂Cl₂ / 0.08 h / 0 °C

2.1: 91 percent / AsPh₃; CuI / Pd₂(dba)3 / dimethylformamide / 1 h / 60 °C

3.1: 86 percent / HF*pyridine complex / tetrahydrofuran; pyridine / 72 h / 0 °C

With copper(l) iodide; triphenyl-arsane; tri-n-butyl-tin hydride; pyridine hydrogenfluoride; bis-triphenylphosphine-palladium(II) chloride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide; 2.1: Stille coupling;

DOI:10.1021/jo0708442

upstream raw materials:

[2-(trimethylsilyl)ethoxy]methyl (1S,2R,3Z,5S,6R,7S,10R,13R)-5-[(1E,3E,5S,6R,7E,12R)-(12-hydroxy-7-methoxycarbonyl-6-methoxymethoxy-5-methyl)trideca-1,3,7-trienyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylate

(1S,2R,3Z,5S,6R,7S,10R,13R)-5-ethynyl-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylic acid

[2-(trimethylsilyl)ethoxy]methyl (1S,2R,5S,6R,7S,10R,13R)-5-ethynyl-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylate

[2-(trimethylsilyl)ethoxy]methyl (1S,2R,5S,6R,7S,10R,13R)-5-[(E)-2-iodoethenyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.0^2,7]tetradec-3-ene-6-carboxylate

Downstream raw materials:

methyl (1S,2E,4E,6S,7R,8Z,13R,16R,17S,20R,23R,25S,26R,27Z)-7-methoxymethoxy-6,13,16,28-tetramethyl-15-oxo-23-phenyl-14,22,24-trioxatetracyclo[14.12.0.0^17,26.0^20,25]octacosa-2,4,8,27-tetraene-8-carboxylate

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