2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

Base Information

Chemical Name:2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione
CAS No.:1377418-93-3
Molecular Formula:C₂₅H₄₄O₃Si
Molecular Weight:420.708
Hs Code.:

Synonyms:2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

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Chemical Property of 2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

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Technology Process of 2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

There total 8 articles about 2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione 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: 73.0%

: 1377419-05-0
2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)cyclohexane-1,3-dione

: 74-88-4
methyl iodide

: 1377418-93-3
2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

Guidance literature:: 2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)cyclohexane-1,3-dione; With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide; In tetrahydrofuran; at 20 ℃; for 0.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at 80 ℃; for 14h; Inert atmosphere;
DOI:10.1002/anie.201200515

Reference yield:

: (3R,5R)-3-(tert-butyldimethylsilyloxy)-5-isopropyl-2-methylcyclopent-1-enecarbaldehyde

: 1377418-93-3
2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

Guidance literature:: Multi-step reaction with 5 steps

1.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

2.1: mercury(II) diacetate / 24 h / 60 °C / Inert atmosphere

3.1: toluene / 16 h / 173 °C / Inert atmosphere

4.1: L-proline / dichloromethane / 3 h / 20 °C / Inert atmosphere

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

5.2: 14 h / 80 °C / Inert atmosphere

With sodium tetrahydroborate; mercury(II) diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; toluene; 3.1: Claisen rearrangement / 4.1: Knoevenagel condensation / 5.1: Heck reaction / 5.2: Heck reaction;
DOI:10.1002/anie.201200515

Reference yield:

: 6485-40-1,2244-16-8
(R)-Carvone

: 1377418-93-3
2-(2-((1R,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium aluminium tetrahydride / diethyl ether / 0.25 h / -78 °C / Inert atmosphere

2.1: 1H-imidazole / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

3.1: platinum(IV) oxide; hydrogen / tetrahydrofuran / 4 h / 20 °C

4.1: ozone / methanol; dichloromethane / -78 °C

4.2: 1.25 h / -78 - 20 °C

5.1: piperidine; acetic acid / diethyl ether / 20 h / 70 °C / Inert atmosphere

6.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

7.1: mercury(II) diacetate / 24 h / 60 °C / Inert atmosphere

8.1: toluene / 16 h / 173 °C / Inert atmosphere

9.1: L-proline / dichloromethane / 3 h / 20 °C / Inert atmosphere

10.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.2: 14 h / 80 °C / Inert atmosphere

With piperidine; 1H-imidazole; platinum(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; mercury(II) diacetate; hydrogen; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 8.1: Claisen rearrangement / 9.1: Knoevenagel condensation / 10.1: Heck reaction / 10.2: Heck reaction;
DOI:10.1002/anie.201200515