[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

Base Information

• Chemical Name: [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
• CAS No.: 948995-42-4
• Molecular Formula: C₂₉H₄₀O₅Si
• Molecular Weight: 496.719

Synonyms:[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

Chemical Property of [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

Chemical Property:

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Technology Process of [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

There total 1 articles about [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 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: 92.0%

(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) + (2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) → [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)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1021/jo0708442

Reference yield: 73.0%

[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) → [2-(trimethylsilyl)ethoxy]methyl (1S,2R,5S,6R,7S,10R,13R)-5-[(E)-2-iodoethenyl]-4,6-dimethyl-13-phenyl-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylate (948995-43-5)

Guidance literature:

[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; With tri-n-butyl-tin hydride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; for 0.333333h;

With iodine; In dichloromethane; at 0 ℃; for 0.0833333h; Further stages.;

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) → [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)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jo0708442

upstream raw materials:

(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-trimethylethylsilylethoxy)methyl chloride

Downstream raw materials:

[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

[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-[(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

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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