4,6-Dodecadien-3-one, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[3-[(1S)-1-[[(1,1-dimethylethyl )dimethylsilyl]oxy]-3-butynyl]phenyl]-1-hydroxy-, (1R,4E,6E,11R)-

Base Information

• Chemical Name: 4,6-Dodecadien-3-one, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[3-[(1S)-1-[[(1,1-dimethylethyl )dimethylsilyl]oxy]-3-butynyl]phenyl]-1-hydroxy-, (1R,4E,6E,11R)-
• CAS No.: 667419-34-3
• Molecular Formula: C34H56O4Si2
• Molecular Weight: 584.987

Synonyms:

Chemical Property of 4,6-Dodecadien-3-one, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[3-[(1S)-1-[[(1,1-dimethylethyl )dimethylsilyl]oxy]-3-butynyl]phenyl]-1-hydroxy-, (1R,4E,6E,11R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-Dodecadien-3-one, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[3-[(1S)-1-[[(1,1-dimethylethyl )dimethylsilyl]oxy]-3-butynyl]phenyl]-1-hydroxy-, (1R,4E,6E,11R)-

There total 23 articles about 4,6-Dodecadien-3-one, 11-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[3-[(1S)-1-[[(1,1-dimethylethyl )dimethylsilyl]oxy]-3-butynyl]phenyl]-1-hydroxy-, (1R,4E,6E,11R)- 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: 83.0%

(1R,4E,6E,11R)-11-(tert-butyldimethylsilyloxy)-1-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-1-triethylsilyloxy-4,6-dodecadien-3-one (850005-80-0) → (4E,6E)-(1R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-1-hydroxy-dodeca-4,6-dien-3-one (667419-34-3)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

1,7-heptandiol (629-30-1) → (4E,6E)-(1R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-1-hydroxy-dodeca-4,6-dien-3-one (667419-34-3)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 50 percent / sodium hydride / dimethylformamide / 0 °C

2.1: 93 percent / oxalyl chloride; DMSO / CH₂Cl₂ / 1.5 h / -78 °C

3.1: (+)-TADDOL; Ti(O-i-Pr)4 / toluene; hexane / 12 h / -25 °C

4.1: triethylamine; DMAP / CH₂Cl₂ / 20 h / 20 °C

5.1: water; DDQ / CH₂Cl₂ / 1 h / 20 °C

6.1: 2-iodoxybenzoic acid / tetrahydrofuran; dimethylsulfoxide / 0.5 h / 20 °C

7.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / -78 °C

7.2: tetrahydrofuran / -78 - 20 °C

8.1: potassium hydroxide / methanol / 3 h / 20 °C

9.1: imidazole / dimethylformamide / 2 h / 20 °C

10.1: ethylmagnesium bromide / tetrahydrofuran / 0.5 h / 20 °C

10.2: 70 percent / tetrahydrofuran / 2 h / 20 °C

11.1: 49 percent / 1,4-bis(diphenylphosphino)butane / tetrahydrofuran; toluene / 6 h / 20 °C

12.1: 83 percent / AcOH; H₂O / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; dmap; potassium hydroxide; oxalyl dichloride; ethylmagnesium bromide; potassium tert-butylate; water; sodium hydride; (S,S)-taddol; acetic acid; dimethyl sulfoxide; triethylamine; 1,4-di(diphenylphosphino)-butane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2005.01.062

Reference yield:

(R)-(-)-8-Nonin-2-ol (156647-91-5) → (4E,6E)-(1R,11R)-11-(tert-Butyl-dimethyl-silanyloxy)-1-{3-[(S)-1-(tert-butyl-dimethyl-silanyloxy)-but-3-ynyl]-phenyl}-1-hydroxy-dodeca-4,6-dien-3-one (667419-34-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: imidazole / dimethylformamide / 2 h / 20 °C

2.1: ethylmagnesium bromide / tetrahydrofuran / 0.5 h / 20 °C

2.2: 70 percent / tetrahydrofuran / 2 h / 20 °C

3.1: 49 percent / 1,4-bis(diphenylphosphino)butane / tetrahydrofuran; toluene / 6 h / 20 °C

4.1: 83 percent / AcOH; H₂O / tetrahydrofuran / 24 h / 20 °C

With 1H-imidazole; ethylmagnesium bromide; water; acetic acid; 1,4-di(diphenylphosphino)-butane; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2005.01.062

upstream raw materials:

(1R,4E,6E,11R)-11-(tert-butyldimethylsilyloxy)-1-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-1-triethylsilyloxy-4,6-dodecadien-3-one

Isophthalaldehyde

1,7-heptandiol

3-(hydroxymethyl)benzaldehyde

Downstream raw materials:

(2Z,4E,7S)-7-tert-butyldimethylsilyloxy-7-[3-[(4R,6R)-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)-nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxan-4-yl]]phenylhepta-2,4-dienoic acid ethyl ester

(2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-(1-methoxy-1-methyl-ethoxy)-hepta-2,4-dienoic acid ethyl ester

(2Z,4E)-(S)-7-(3-{(4R,6R)-6-[(1E,3E)-(R)-8-(tert-Butyl-dimethyl-silanyloxy)-nona-1,3-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-phenyl)-7-hydroxy-hepta-2,4-dienoic acid ethyl ester

(4R,6R)-4-[3-[(1S)-1-(tert-butyldimethylsilyloxy)-3-butynyl]phenyl]-6-[(1E,3E,8R)-8-(tert-butyldimethylsilyloxy)nona-1,3-dienyl]-2,2-dimethyl-1,3-dioxane

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