(S)-Debromoneoaplaminone

Base Information

• Chemical Name: (S)-Debromoneoaplaminone
• CAS No.: 143654-12-0
• Molecular Formula: C₂₆H₄₁NO₄
• Molecular Weight: 431.616
• Mol file: 143654-12-0.mol

Synonyms:

Chemical Property of (S)-Debromoneoaplaminone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-Debromoneoaplaminone

There total 18 articles about (S)-Debromoneoaplaminone 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:

(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) → (S)-Debromoneoaplaminone (143654-12-0)

Guidance literature:

With acetic acid; at 60 ℃;

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

Reference yield:

4-allylguaiacol (97-53-0) → (S)-Debromoneoaplaminone (143654-12-0)

Guidance literature:

Multi-step reaction with 14 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

13: MnO₂ / CH₂Cl₂ / 23 °C

14: aq. AcOH / 60 °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; acetic acid; dimethyl sulfoxide; dimethyl amine; triethylamine; sodium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; 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) → (S)-Debromoneoaplaminone (143654-12-0)

Guidance literature:

Multi-step reaction with 9 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

8: MnO₂ / CH₂Cl₂ / 23 °C

9: aq. AcOH / 60 °C

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

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

upstream raw materials:

(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

4-allylguaiacol

(4S)-5-{[(tert-butyl)dimethylsilyl]oxy}-4-methylpentan-1-ol

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

Refernces