(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

Base Information

Chemical Name:(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol
CAS No.:1585153-98-5
Molecular Formula:C₂₄H₃₆O₃
Molecular Weight:372.548
Hs Code.:

Synonyms:(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

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Chemical Property of (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

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Technology Process of (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

There total 12 articles about (2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol 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:

: 1585153-95-2
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-one

: 1585153-97-4
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

: 1585153-98-5
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

Guidance literature:: With borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene; at 0 ℃; for 0.0833333h; Overall yield = 71 %; Overall yield = 3.56 g; Inert atmosphere;
DOI:10.1021/ol500553x

Reference yield:

: 106-24-1
Geraniol

: 1585153-97-4
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

: 1585153-98-5
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: pyridine / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere

2.1: (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; dihydrogen peroxide / acetonitrile / 72 h / -15 °C / Inert atmosphere

3.1: sodium methylate; tetra-(n-butyl)ammonium iodide / methanol / 2.5 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

5.1: lithium bromide / tetrahydrofuran; dichloromethane / 2.5 h / Inert atmosphere; Cooling

6.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

6.2: 3 h / -78 - 20 °C / Inert atmosphere

7.1: calcium carbonate; iodine / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

8.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / tetrahydrofuran; dichloromethane; toluene / 0.08 h / 0 °C / Inert atmosphere

With pyridine; n-butyllithium; borane-THF; dihydrogen peroxide; iodine; sodium methylate; tetra-(n-butyl)ammonium iodide; triethylamine; (3aS,4'R,7aS)-2,2,2',2'-tetramethyldihydrospiro[[1,3]dioxolo-[4,5-c]pyran-6,4'-[1,3]dioxolan]-7(7aH)-one; calcium carbonate; lithium bromide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; acetonitrile; 2.1: |Shi Asymmetric Epoxidation;
DOI:10.1021/ol500553x

Reference yield:

: 2944-49-2
2,3-dimethylanisole

: 1585153-97-4
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

: 1585153-98-5
(2E,6E)-9-((S)-3,3-dimethyloxiran-2-yl)-1-(4-methoxy-2,3-dimethylphenyl)-3,7-dimethylnona-2,6-dien-4-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: N-Bromosuccinimide / acetonitrile / 3 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Irradiation

2.2: 2.5 h / -78 - 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / hexane; dichloromethane / -78 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

7.1: boron trifluoride diethyl etherate / dichloromethane / 3 h / 0 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

8.2: 3 h / -78 - 20 °C / Inert atmosphere

9.1: calcium carbonate; iodine / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

10.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; borane-THF / tetrahydrofuran; dichloromethane; toluene / 0.08 h / 0 °C / Inert atmosphere

With N-Bromosuccinimide; n-butyllithium; borane-THF; boron trifluoride diethyl etherate; iodine; diisobutylaluminium hydride; Dess-Martin periodane; calcium carbonate; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; hexane; dichloromethane; water; toluene; acetonitrile; 4.1: |Wittig Olefination;
DOI:10.1021/ol500553x