(3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol

Base Information

• Chemical Name: (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol
• CAS No.: 143654-09-5
• Molecular Formula: C₃₄H₆₁NO₅Si
• Molecular Weight: 591.948
• Mol file: 143654-09-5.mol

Synonyms:

Chemical Property of (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol

There total 30 articles about (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-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:

4-allylguaiacol (97-53-0) → (3E,10E)-(R)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol (143654-09-5,143654-16-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 78 percent / NaH / tetrahydrofuran / 3 h / 23 °C

2: 1.) O₃/O₂, 2.) Me₂S / 1.) MeOH, -78 deg C, 2 h, 2.) -78 deg C to 23 deg C, 3.5 h

3: KMnO₄, 1 M phosphate buffer (pH 7) / 2-methyl-propan-2-ol / 0.17 h / 23 °C

4: tetrahydrofuran / 1 h / 50 °C

5: 50 percent Me₂NH / 0.17 h / 23 °C

6: LiAlH₄ / diethyl ether / 0.5 h / 23 °C

7: 1a.) Pd(OAc)2, 1b.) NaCl, 2.) Et₃N / 1a.) benzene, 23 deg C, 86 h, 1b.) acetone, H₂O, 23 deg C, 4 h, 2.) toluene, reflux, 1 h

8: 1.) Li (1 percent Na) / 1.) ether, -50 deg C to 23 deg C, 1.5 h, 2.) THF, -78 deg C, 10 min

9: 40 percent / Na, liquid NH₃ / tetrahydrofuran / 0.17 h / -78 °C

10: Bu₄NF / tetrahydrofuran / 14 h / 23 °C

11: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 15 min, 2.) -65 deg C to 23 deg C, 20 min

12: 1.) n-BuLi / 1a.) THF, -78 deg C, 20 min, 1b.) -50 deg C, 1 h, 2.) -78 deg C, 10 min

With palladium diacetate; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; phosphate buffer; oxalyl dichloride; dimethylsulfide; lithium (1 percent sodium); tetrabutyl ammonium fluoride; ammonia; oxygen; sodium; sodium hydride; ozone; dimethyl sulfoxide; dimethyl amine; triethylamine; sodium chloride; In tetrahydrofuran; diethyl ether; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74687-9

Reference yield:

4-allylguaiacol (97-53-0) → (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol (143654-09-5,143654-16-4)

Guidance literature:

Multi-step reaction with 12 steps

1: 78 percent / NaH / tetrahydrofuran / 3 h / 23 °C

2: 1.) O₃/O₂, 2.) Me₂S / 1.) MeOH, -78 deg C, 2 h, 2.) -78 deg C to 23 deg C, 3.5 h

3: KMnO₄, 1 M phosphate buffer (pH 7) / 2-methyl-propan-2-ol / 0.17 h / 23 °C

4: tetrahydrofuran / 1 h / 50 °C

5: 50 percent Me₂NH / 0.17 h / 23 °C

6: LiAlH₄ / diethyl ether / 0.5 h / 23 °C

7: 1a.) Pd(OAc)2, 1b.) NaCl, 2.) Et₃N / 1a.) benzene, 23 deg C, 86 h, 1b.) acetone, H₂O, 23 deg C, 4 h, 2.) toluene, reflux, 1 h

8: 1.) Li (1 percent Na) / 1.) ether, -50 deg C to 23 deg C, 2.) THF, -78 deg C

9: Na, liquid NH₃ / tetrahydrofuran / -78 °C

10: Bu₄NF / tetrahydrofuran / 23 °C

11: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 2.) -65 deg C to 23 deg C

12: 1.) n-BuLi / 1a.) THF, -78 deg C, 1b.) -50 deg C, 2.) -78 deg C

With palladium diacetate; potassium permanganate; lithium aluminium tetrahydride; n-butyllithium; phosphate buffer; oxalyl dichloride; dimethylsulfide; lithium (1 percent sodium); tetrabutyl ammonium fluoride; ammonia; oxygen; sodium; sodium hydride; ozone; dimethyl sulfoxide; dimethyl amine; triethylamine; sodium chloride; In tetrahydrofuran; diethyl ether; tert-butyl alcohol;

DOI:10.1016/S0040-4039(00)74687-9

Reference yield:

(4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methylpentan-1-ol (105859-48-1) → (3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-ol (143654-09-5,143654-16-4)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 23 °C

2: LiCl, CaCO₃ / butan-2-one / Heating

3: 1.) Li (1 percent Na) / 1.) ether, -50 deg C to 23 deg C, 2.) THF, -78 deg C

4: Na, liquid NH₃ / tetrahydrofuran / -78 °C

5: Bu₄NF / tetrahydrofuran / 23 °C

6: 1.) DMSO, (COCl)2, 2.) Et₃N / 1.) CH₂Cl₂, -65 deg C, 2.) -65 deg C to 23 deg C

7: 1.) n-BuLi / 1a.) THF, -78 deg C, 1b.) -50 deg C, 2.) -78 deg C

With pyridine; n-butyllithium; oxalyl dichloride; lithium (1 percent sodium); tetrabutyl ammonium fluoride; ammonia; sodium; dimethyl sulfoxide; triethylamine; calcium carbonate; lithium chloride; In tetrahydrofuran; butanone;

DOI:10.1016/S0040-4039(00)74687-9

upstream raw materials:

3-methyl-1-(tri-n-butylstannyl)-3-[(triethylsilyl)oxy]but-1(E)-ene

(E)-(R)-8-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6-dimethyl-oct-6-enal

4-allylguaiacol

4-allyl-2-methoxy-1-(methoxymethoxy)benzene

Downstream raw materials:

(S)-Debromoneoaplaminone

(R)-debromoneoaplaminone

(3E,10E)-(S)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-one

(3E,10E)-(R)-12-[2-(2-Dimethylamino-ethyl)-4-methoxy-5-methoxymethoxy-phenyl]-2,6,10-trimethyl-2-triethylsilanyloxy-dodeca-3,10-dien-5-one

Refernces