(1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane

Base Information

• Chemical Name: (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane
• CAS No.: 277334-09-5
• Molecular Formula: C₃₁H₄₈O₃Si
• Molecular Weight: 496.806

Synonyms:(1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane

Chemical Property of (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane

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Technology Process of (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane

There total 6 articles about (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane 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: 38.0%

trimethylsilyl iodide (16029-98-4) + 2-{[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-(4E)-4-pentenyl}cyclohexanone (277334-06-2) → 1-(trimethylsiloxy)-2-{[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexylcarbonyl]-(4E)-4-pentenyl}cyclohexene + (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.03,7]undecane (277334-09-5) + (1S,2R,3R,7R)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.03,7]undecane (277334-08-4)

Guidance literature:

With 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4039(00)00101-5

Reference yield:

(1S,2R,3R,7R)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.03,7]undecane (277334-08-4) → 1-(trimethylsiloxy)-2-{[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexylcarbonyl]-(4E)-4-pentenyl}cyclohexene + (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.03,7]undecane (277334-09-5)

Guidance literature:

With trimethylsilyl iodide; 1,1,1,3,3,3-hexamethyl-disilazane; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)00101-5

Reference yield:

cyclohexanone N-cyclohexylimine (10468-40-3) → (1R,2S,3S,7S)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.03,7]undecane (277334-09-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: i-PrNH₂; BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

1.2: 86 percent / hexane; tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 0 °C

2.1: (CO₂H)2*2H₂O / tetrahydrofuran; H₂O / 4 h / 20 °C

3.1: 3.36 g / acetonitrile / 13 h / 20 °C

4.1: 6 percent / HMDS / CH₂Cl₂ / 1 h / 20 °C

With n-butyllithium; oxalic acid; isopropylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; 3.1: Wittig reaction;

DOI:10.1021/jo010207q

upstream raw materials:

trimethylsilyl iodide

2-{[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-(4E)-4-pentenyl}cyclohexanone

(1S,2R,3R,7R)-2-[(1R,2S,5R)-2-(1-methyl-1-phenylethyl)-5-methylcyclohexyloxycarbonyl]-1-(trimethylsiloxy)tricyclo[5.4.0.0^3,7]undecane

cyclohexanone N-cyclohexylimine

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