(4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate

Base Information

• Chemical Name: (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate
• CAS No.: 1377418-98-8
• Molecular Formula: C₃₁H₅₅F₃O₆SSi₂
• Molecular Weight: 669.006

Synonyms:

Chemical Property of (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate

There total 16 articles about (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate 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:

(4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methylcyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate (1377419-09-4) → (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate (1377418-98-8)

Guidance literature:

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; In dichloromethane; at 20 ℃; regioselective reaction; Inert atmosphere;

DOI:10.1002/anie.201200515

Reference yield:

(3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-6-oxoheptanal → (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate (1377418-98-8)

Guidance literature:

Multi-step reaction with 14 steps

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

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

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

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

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

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.2: 14 h / 80 °C / Inert atmosphere

7.1: ozone / dichloromethane / -78 °C

7.2: 0.5 h / -78 - 20 °C

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

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

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

11.1: sodium tetrahydroborate / methanol / 0.33 h / 0 °C / Inert atmosphere

12.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

13.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

13.2: 3 h / -78 - 20 °C / Inert atmosphere

14.1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 20 °C / Inert atmosphere

With piperidine; pyridine; 2,6-dimethylpyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; lithium carbonate; potassium hexamethylsilazane; 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; 4.1: Claisen rearrangement / 5.1: Knoevenagel condensation / 6.1: Heck reaction / 6.2: Heck reaction / 8.1: Luche reduction;

DOI:10.1002/anie.201200515

Reference yield:

(4R,6R)-carveol (99-48-9,1197-06-4,1197-07-5,2102-58-1,2102-59-2,5157-78-8,5503-11-7,7632-16-8,18383-51-2,22567-18-6,20307-86-2) → (4R,5S)-4-((tert-butyldimethylsilyl)oxy)-5-(2-((1R,6S)-6-((tertbutyldimethylsilyl)oxy)-1-methyl-4-oxocyclohex-2-en-1-yl)ethyl)-2-isopropyl-5-methylcyclopent-1-en-1-yl trifluoromethanesulfonate (1377418-98-8)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 1H-imidazole / dichloromethane / 1.5 h / 0 - 20 °C / Inert atmosphere

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

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

3.2: 1.25 h / -78 - 20 °C

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

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

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

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

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

9.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

9.2: 14 h / 80 °C / Inert atmosphere

10.1: ozone / dichloromethane / -78 °C

10.2: 0.5 h / -78 - 20 °C

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

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

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

14.1: sodium tetrahydroborate / methanol / 0.33 h / 0 °C / Inert atmosphere

15.1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C / Inert atmosphere

16.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 1 h / -40 °C / Inert atmosphere

16.2: 3 h / -78 - 20 °C / Inert atmosphere

17.1: 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide / dichloromethane / 20 °C / Inert atmosphere

With piperidine; pyridine; 1H-imidazole; 2,6-dimethylpyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; dmap; platinum(IV) oxide; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; hydrogen; lithium carbonate; potassium hexamethylsilazane; 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; 7.1: Claisen rearrangement / 8.1: Knoevenagel condensation / 9.1: Heck reaction / 9.2: Heck reaction / 11.1: Luche reduction;

DOI:10.1002/anie.201200515

upstream raw materials:

2-((1R,3R,5R)-5-(tert-butyldimethylsilyloxy)-3-isopropyl-1-methyl-2-methylenecyclopentyl)acetaldehyde

tert-butyl((1R,4R)-4-isopropyl-2-methyl-3-(vinyloxymethyl)cyclopent-2-enyloxy)dimethylsilane

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

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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