aspidospermine

Base Information

• Chemical Name: aspidospermine
• CAS No.: 88198-98-5
• Molecular Formula: C₂₂H₃₀N₂O₂
• Molecular Weight: 354.492
• Mol file: 88198-98-5.mol

Synonyms:aspidospermine

Chemical Property of aspidospermine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of aspidospermine

There total 60 articles about aspidospermine 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:

C35H36N2O5 → aspidospermine (88198-98-5) + aspidospermine (466-49-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ammonia / methanol / 3.5 h / 0 - 70 °C

2.1: pyridine; trifluoroacetic anhydride / 1,4-dioxane / 16 h / 0 - 20 °C

3.1: acetyl chloride / methanol / 0.5 h / 23 °C / Inert atmosphere

3.2: 2 h / 23 °C / Inert atmosphere

4.1: sodium tri-sec-butylborohydride / tetrahydrofuran / 2 h / 23 °C

5.1: di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid / toluene / 5 h / 23 °C

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 23 - 70 °C / Reflux

7.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 3.17 h / 23 °C

8.1: pyridine / 18 h / 23 °C

8.2: 2 h / Inert atmosphere

9.1: methanol; diethyl ether; toluene / 64 h

10.1: chiralcel AD / hexane; isopropyl alcohol

With pyridine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; ammonia; hydrogen; sodium tri-sec-butylborohydride; acetyl chloride; triphenylphosphine; trifluoroacetic anhydride; 4-nitro-benzoic acid; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol300599p

Reference yield:

C34H33N3O3 → aspidospermine (88198-98-5) + aspidospermine (466-49-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: acetyl chloride / methanol / 0.5 h / 23 °C / Inert atmosphere

1.2: 2 h / 23 °C / Inert atmosphere

2.1: sodium tri-sec-butylborohydride / tetrahydrofuran / 2 h / 23 °C

3.1: di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid / toluene / 5 h / 23 °C

4.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 23 - 70 °C / Reflux

5.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 3.17 h / 23 °C

6.1: pyridine / 18 h / 23 °C

6.2: 2 h / Inert atmosphere

7.1: methanol; diethyl ether; toluene / 64 h

8.1: chiralcel AD / hexane; isopropyl alcohol

With pyridine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium tri-sec-butylborohydride; acetyl chloride; triphenylphosphine; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol300599p

Reference yield:

C34H35N3O3 → aspidospermine (88198-98-5) + aspidospermine (466-49-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium tri-sec-butylborohydride / tetrahydrofuran / 2 h / 23 °C

2.1: di-isopropyl azodicarboxylate; triphenylphosphine; 4-nitro-benzoic acid / toluene / 5 h / 23 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 5 h / 23 - 70 °C / Reflux

4.1: palladium 10% on activated carbon; hydrogen / methanol; dichloromethane / 3.17 h / 23 °C

5.1: pyridine / 18 h / 23 °C

5.2: 2 h / Inert atmosphere

6.1: methanol; diethyl ether; toluene / 64 h

7.1: chiralcel AD / hexane; isopropyl alcohol

With pyridine; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; palladium 10% on activated carbon; hydrogen; sodium tri-sec-butylborohydride; triphenylphosphine; 4-nitro-benzoic acid; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; isopropyl alcohol; toluene;

DOI:10.1021/ol300599p

upstream raw materials:

acetic anhydride

diazomethyl-trimethyl-silane

C₂₃H₁₉NO₂

C₂₄H₂₄N₂O

Downstream raw materials:

aspidospermine

Refernces

• 1、 Lajiness, James P.,Jiang, Wanlong,Boger, Dale L.. "Divergent total syntheses of (-)-aspidospermine and (+)-spegazzinine". . p. 2078 - 2081. Retrieved 2012/06/18.