(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

Base Information

• Chemical Name: (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
• CAS No.: 143654-10-8
• Molecular Formula: C₃₄H₅₉NO₅Si
• Molecular Weight: 589.932
• Mol file: 143654-10-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 34 articles about (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 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: 72.0%

(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) → (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 (143654-10-8)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 23 ℃; for 14h;

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

Reference yield:

(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) → (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 (143654-10-8)

Guidance literature:

With manganese(IV) oxide; In dichloromethane; at 23 ℃;

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

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-one (143654-10-8)

Guidance literature:

Multi-step reaction with 13 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

13: 72 percent / MnO₂ / CH₂Cl₂ / 14 h / 23 °C

With manganese(IV) oxide; 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; dichloromethane; tert-butyl alcohol;

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

upstream raw materials:

(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

4-allylguaiacol

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

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

Downstream raw materials:

(R)-debromoneoaplaminone

(S)-Debromoneoaplaminone

Refernces