(4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene

Base Information

• Chemical Name: (4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene
• CAS No.: 135619-53-3
• Molecular Formula: C₁₉H₂₂O₄S
• Molecular Weight: 346.447

Synonyms:(4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene

Chemical Property of (4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene

Chemical Property:

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Technology Process of (4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene

There total 3 articles about (4R^*,10R^*,13S^*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridec-1-ene 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:

3-(phenylsulfonyl)-2-cycloocten-1-yl 2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butenoate (135619-70-4,135619-71-5) → (4R*,10R*,13S*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.04,13>tridec-1-ene (135619-53-3) + (1S*,4S*,10R*,13S*)-12-methylene-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.04,13>tridecane (135619-52-2,135683-32-8) + (1R*,4R*,10R*,13R*)-12-methylene-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.04,13>tridecane (135619-52-2,135683-32-8)

Guidance literature:

With palladium diacetate; triisopropyl phosphite; In 1,4-dioxane; at 100 ℃; for 0.666667h;

DOI:10.1021/ja00019a037

Reference yield:

2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butenoic acid (135619-58-8) → (4R*,10R*,13S*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.04,13>tridec-1-ene (135619-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 66 percent / DMAP, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / Ambient temperature

2: 49.1 mg / Pd(CH₃COO)2, (i-PrO)3P / dioxane / 0.67 h / 100 °C

With dmap; palladium diacetate; triisopropyl phosphite; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja00019a037

Reference yield:

1,1,1-tris(phenylthio)-2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butene (135619-37-3) → (4R*,10R*,13S*)-12-methyl-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.04,13>tridec-1-ene (135619-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 64 percent / CF₃COOAg, H₂O / dioxane / 6 h / Heating

2: 66 percent / DMAP, N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 2 h / Ambient temperature

3: 49.1 mg / Pd(CH₃COO)2, (i-PrO)3P / dioxane / 0.67 h / 100 °C

With dmap; palladium diacetate; triisopropyl phosphite; water; silver trifluoroacetate; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane;

DOI:10.1021/ja00019a037

upstream raw materials:

3-(phenylsulfonyl)-2-cycloocten-1-yl 2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butenoate

2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butenoic acid

1,1,1-tris(phenylthio)-2-<(methoxycarbonyl)oxy>-3-<(trimethylsilyl)methyl>-3-butene

Downstream raw materials:

(1S^*,4S^*,10R^*,13S^*)-12-methylene-10-(phenylsulfonyl)-2-oxo-3-oxatricyclo<8.2.1.0^4,13>tridecane

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