1-Acetyl-19,21-epoxyaspidospermidine

Base Information

• Chemical Name: 1-Acetyl-19,21-epoxyaspidospermidine
• CAS No.: 2671-45-6
• Molecular Formula: C21H26N2O2
• Molecular Weight: 338.44
• Mol file: 2671-45-6.mol

Synonyms:1-Acetyl-19,21-epoxyaspidospermidine;N-Acetylaspidoalbidine

Chemical Property of 1-Acetyl-19,21-epoxyaspidospermidine

Chemical Property:

• PSA: 32.78000
• LogP: 3.05870

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Acetyl-19,21-epoxyaspidospermidine

There total 21 articles about 1-Acetyl-19,21-epoxyaspidospermidine 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: 100.0%

(+)-fendleridine (36459-35-5) + acetic anhydride (108-24-7) → 1-Acetyl-aspidoalbidin (2671-45-6,56197-21-8)

Guidance literature:

With pyridine; In dichloromethane; at 23 ℃; Inert atmosphere;

DOI:10.1021/acs.joc.9b00145

Reference yield:

n-decyl 2-vinylbut-(2)-enoate → 1-Acetyl-aspidoalbidin (2671-45-6,56197-21-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diisopropylamine; n-butyllithium; 1,3,4-trimethylimidazolidin-2-one / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 14 h / 23 °C / Inert atmosphere; Cooling with ice

2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 6 h / 0 - 23 °C / Inert atmosphere

3.1: sodium hydroxide / methanol; water / 40 h / 100 °C / Inert atmosphere; Sealed tube

4.1: N-ethyl-N,N-diisopropylamine; triphenylphosphine / dichloromethane / 16 h / -5 - 23 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 18 h / 80 °C / Inert atmosphere; Sealed tube

6.1: palladium diacetate; p-benzoquinone; perchloric acid / acetonitrile; toluene / 6 h / 23 °C / Inert atmosphere

7.1: sodium tetrahydroborate / acetonitrile; toluene / 2 h / Inert atmosphere

8.1: triethylamine; Candida rugosa lipase / toluene / 6 h / 23 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction

9.1: platinum(IV) oxide; hydrogen / methanol; ethyl acetate / 16 h / 23 °C

10.1: dmap / dichloromethane / 12 h / Inert atmosphere

11.1: tri-n-butyl-tin hydride; trifluoromethylsulfonic anhydride / acetonitrile / 2.33 h / -40 - 23 °C / Inert atmosphere

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol; acetonitrile / 13 h / Inert atmosphere

13.1: trifluoroacetic acid; thiophenol / 5.5 h / 55 °C / Inert atmosphere

13.2: 12 h / Inert atmosphere

14.1: pyridine / dichloromethane / 6 h / 23 °C / Inert atmosphere

With pyridine; triethylsilane; dmap; 1,3,4-trimethylimidazolidin-2-one; platinum(IV) oxide; sodium tetrahydroborate; n-butyllithium; perchloric acid; Hoveyda-Grubbs catalyst second generation; trifluoromethylsulfonic anhydride; hydrogen; tri-n-butyl-tin hydride; palladium diacetate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; p-benzoquinone; sodium hydroxide; Candida rugosa lipase; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; acetonitrile; 6.1: |Wacker-Tsuji Olefin Oxidation;

DOI:10.1021/jacs.6b07623

Reference yield:

C18H18INO → 1-Acetyl-aspidoalbidin (2671-45-6,56197-21-8)

Guidance literature:

Multi-step reaction with 14 steps

1.1: diisopropylamine; n-butyllithium; 1,3,4-trimethylimidazolidin-2-one / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 14 h / 23 °C / Inert atmosphere; Cooling with ice

2.1: trifluoroacetic acid; triethylsilane / dichloromethane / 6 h / 0 - 23 °C / Inert atmosphere

3.1: sodium hydroxide / methanol; water / 40 h / 100 °C / Inert atmosphere; Sealed tube

4.1: N-ethyl-N,N-diisopropylamine; triphenylphosphine / dichloromethane / 16 h / -5 - 23 °C / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / 1,2-dichloro-ethane / 18 h / 80 °C / Inert atmosphere; Sealed tube

6.1: palladium diacetate; p-benzoquinone; perchloric acid / acetonitrile; toluene / 6 h / 23 °C / Inert atmosphere

7.1: sodium tetrahydroborate / acetonitrile; toluene / 2 h / Inert atmosphere

8.1: triethylamine; Candida rugosa lipase / toluene / 6 h / 23 °C / Inert atmosphere; Resolution of racemate; Enzymatic reaction

9.1: platinum(IV) oxide; hydrogen / methanol; ethyl acetate / 16 h / 23 °C

10.1: dmap / dichloromethane / 12 h / Inert atmosphere

11.1: tri-n-butyl-tin hydride; trifluoromethylsulfonic anhydride / acetonitrile / 2.33 h / -40 - 23 °C / Inert atmosphere

12.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / methanol; acetonitrile / 13 h / Inert atmosphere

13.1: trifluoroacetic acid; thiophenol / 5.5 h / 55 °C / Inert atmosphere

13.2: 12 h / Inert atmosphere

14.1: pyridine / dichloromethane / 6 h / 23 °C / Inert atmosphere

With pyridine; triethylsilane; dmap; 1,3,4-trimethylimidazolidin-2-one; platinum(IV) oxide; sodium tetrahydroborate; n-butyllithium; perchloric acid; Hoveyda-Grubbs catalyst second generation; trifluoromethylsulfonic anhydride; hydrogen; tri-n-butyl-tin hydride; palladium diacetate; thiophenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; p-benzoquinone; sodium hydroxide; Candida rugosa lipase; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 1,2-dichloro-ethane; toluene; acetonitrile; 6.1: |Wacker-Tsuji Olefin Oxidation;

DOI:10.1021/jacs.6b07623

upstream raw materials:

(+)-fendleridine

acetic anhydride

Refernces

• 1、 Ghosh, Arun K.,Born, Joshua R.,Kassekert, Luke A.. "Enantioselective Total Syntheses of (+)-Fendleridine and (+)-Acetylaspidoalbidine". . p. 5167 - 5175. Retrieved 2019/05/10.