(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

Base Information

• Chemical Name: (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
• CAS No.: 854490-37-2
• Molecular Formula: C₂₃H₂₆O₄
• Molecular Weight: 366.457

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 1 articles about (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 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:

(2R,4S,5R)-5-[(3E)-4-formylpent-3-enyl]-4-[3-methyl-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane → (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,2S,3Z,5R,6R,7S,10R,13R)-4,6-dimethyl-13-phenyl-5-[2-(trimethylsilyl)ethynyl]-12,14-dioxatricyclo[8.4.0.02,7]tetradec-3-ene-6-carboxylic acid (854490-46-3)

Guidance literature:

(2R,4S,5R)-5-[(3E)-4-formylpent-3-enyl]-4-[3-methyl-6-(trimethylsilyl)hexa-1,3-dien-5-ynyl]-2-phenyl-1,3-dioxane; With 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 80 ℃; for 24h;

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 0 ℃; for 5.5h;

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/ol0507625

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:

(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-(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:

Multi-step reaction with 2 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

With tri-n-butyl-tin hydride; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran;

DOI:10.1021/jo0708442

Downstream raw materials:

[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

[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

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