(+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Base Information

• Chemical Name: (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene
• CAS No.: 136066-63-2
• Molecular Formula: C₂₄H₃₄O₃Si
• Molecular Weight: 398.618

Synonyms:(+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Chemical Property of (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

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Technology Process of (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

There total 4 articles about (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-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: 65.0%

N,O-bis-(trimethylsilyl)-acetamide (10416-59-8) + (+/-)-3-<2-hydroxy-2-methyl-2-(2,4,6-trimethylphenyl)acetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-62-1,136172-33-3) → (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-63-2)

Guidance literature:

at 80 ℃; for 12h;

DOI:10.1021/ja00020a026

Reference yield:

(1S,2R,5S,6R)-Tricyclo[4.2.1.02,5]non-7-en-3-ol (136066-56-3,136173-43-8) → (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-63-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / 1,3-dicyclohexylcarbodiimide (DCC), 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 1 h / 25 °C

2: 76 percent / tetrahydrofuran / 12 h / -70 - 25 °C

3: 65 percent / 12 h / 80 °C

With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00020a026

Reference yield:

3-(2-oxopropionoxy)-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-61-0) → (+/-)-3-<2-methyl-2-(2,4,6-trimethylphenyl)-2-<(trimethylsilyl)oxy>acetoxy>-endo-tricyclo<4.2.1.02,5>non-7-ene (136066-63-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / tetrahydrofuran / 12 h / -70 - 25 °C

2: 65 percent / 12 h / 80 °C

In tetrahydrofuran;

DOI:10.1021/ja00020a026

upstream raw materials:

N,O-bis-(trimethylsilyl)-acetamide

(+/-)-3-<2-hydroxy-2-methyl-2-(2,4,6-trimethylphenyl)acetoxy>-endo-tricyclo<4.2.1.0^2,5>non-7-ene

(1S,2R,5S,6R)-Tricyclo[4.2.1.0^2,5]non-7-en-3-ol

3-(2-oxopropionoxy)-endo-tricyclo<4.2.1.0^2,5>non-7-ene

Downstream raw materials:

(S)-2-(2,4,6-Trimethyl-phenyl)-2-trimethylsilanyloxy-propionic acid (3aR,4S,7aR)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

(S)-2-(2,4,6-Trimethyl-phenyl)-2-trimethylsilanyloxy-propionic acid (3aS,4R,7aS)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

(S)-2-Hydroxy-2-(2,4,6-trimethyl-phenyl)-propionic acid (3aR,4S,7aR)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

(S)-2-Hydroxy-2-(2,4,6-trimethyl-phenyl)-propionic acid (3aS,4R,7aS)-2-ethyl-1,3-dioxo-2,3,3a,4,7,7a-hexahydro-1H-isoindol-4-yl ester

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