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

Base Information

Chemical Name:(1R,2R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methyl-3-oxocyclohexyl methanesulfonate
CAS No.:1377419-07-2
Molecular Formula:C₂₅H₄₆O₆SSi
Molecular Weight:502.788
Hs Code.:

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

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

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

There total 10 articles about (1R,2R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methyl-3-oxocyclohexyl methanesulfonate 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: 88.0%

: 1377418-95-5
(2R,3R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

: 7143-01-3
Methanesulfonic anhydride

: 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

Guidance literature:: With pyridine; dmap; at 20 ℃; for 5h; Inert atmosphere;
DOI:10.1002/anie.201200515

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 8 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

With pyridine; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; ozone; 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 / 7.1: Luche reduction;
DOI:10.1002/anie.201200515

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 13 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

With piperidine; pyridine; 1H-imidazole; dmap; platinum(IV) oxide; sodium tetrahydroborate; lithium aluminium tetrahydride; cerium(III) chloride heptahydrate; 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 / 12.1: Luche reduction;
DOI:10.1002/anie.201200515