(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

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Chemical Name:(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone
CAS No.:1377418-96-6
Molecular Formula:C₂₄H₄₂O₃Si
Molecular Weight:406.681
Hs Code.:

Synonyms:(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

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Chemical Property of (R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

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Technology Process of (R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

There total 12 articles about (R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone 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: 79.0%

: 1377419-07-2
(1R,2R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methyl-3-oxocyclohexyl methanesulfonate

: 1377418-96-6
(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

Guidance literature:: With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 140 ℃; for 1h; Inert atmosphere;
DOI:10.1002/anie.201200515

Reference yield:

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

: 1377418-96-6
(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

Guidance literature:: Multi-step reaction with 9 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

6.1: ozone / dichloromethane / -78 °C

6.2: 0.5 h / -78 - 20 °C

7.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere

8.1: pyridine; dmap / 5 h / 20 °C / Inert atmosphere

9.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 1 h / 140 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; lithium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium bromide; lithium iodide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3.1: Claisen rearrangement / 4.1: Knoevenagel condensation / 5.1: Heck reaction / 5.2: Heck reaction / 7.1: Luche reduction;
DOI:10.1002/anie.201200515

Reference yield:

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

: 1377418-96-6
(R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohex-3-enone

Guidance literature:: Multi-step reaction with 14 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

11.1: ozone / dichloromethane / -78 °C

11.2: 0.5 h / -78 - 20 °C

12.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere

13.1: pyridine; dmap / 5 h / 20 °C / Inert atmosphere

14.1: lithium carbonate; lithium bromide / N,N-dimethyl-formamide / 1 h / 140 °C / Inert atmosphere

With piperidine; pyridine; 1H-imidazole; dmap; platinum(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride heptahydrate; mercury(II) diacetate; hydrogen; lithium carbonate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium bromide; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; 8.1: Claisen rearrangement / 9.1: Knoevenagel condensation / 10.1: Heck reaction / 10.2: Heck reaction / 12.1: Luche reduction;
DOI:10.1002/anie.201200515