(16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester

Base Information

• Chemical Name: (16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester
• CAS No.: 1897-26-3
• Molecular Formula: C23H26N2O4
• Molecular Weight: 394.47

Synonyms:

Chemical Property of (16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester

Chemical Property:

• Melting Point: 160 °C
• Boiling Point: 511.2±50.0 °C(Predicted)
• PKA: 5.35±0.40(Predicted)
• PSA: 68.20000
• Density: 1.35±0.1 g/cm3(Predicted)
• LogP: 2.16060

Purity/Quality:

>=95% ^*data from raw suppliers

Akuammiline 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester

There total 42 articles about (16R)-17-Acetoxyakuammilan-16-carboxylic acid methyl ester 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: 99.0%

acetic anhydride (108-24-7) + (E)-(16R)-17-hydroxy-16-(methoxycarbonyl)-1,2-dehydro-curan-18-ene (1897-30-9) → akuammiline (1897-26-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/anie.201901086

Reference yield:

C32H34N2O5SSi → akuammiline (1897-26-3)

Guidance literature:

Multi-step reaction with 20 steps

1.1: silver trifluoromethanesulfonate; (trimethylphosphine)gold(I) chloride / toluene / 40 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / water / Inert atmosphere

2.2: 65 °C / Inert atmosphere

2.3: -78 - 23 °C / Inert atmosphere

3.1: potassium carbonate; N-iodo-succinimide / 23 °C / Inert atmosphere

4.1: acetic acid / water; tetrahydrofuran / 75 °C / Inert atmosphere

5.1: sodium tetrahydroborate / methanol / 0 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid / benzene / 80 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 40 °C / Inert atmosphere

8.1: trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere

9.1: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 23 °C / Inert atmosphere

10.1: sodium hydroxide / tetrahydrofuran; water / 14 h / 23 °C / Inert atmosphere

11.1: dichloromethane; hexane / 0.5 h / 23 °C / Inert atmosphere

12.1: dmap; triethylamine / dichloromethane / 2 h / 23 °C / Inert atmosphere

13.1: caesium carbonate / acetonitrile / 46 h / 40 °C / Inert atmosphere

14.1: tetrahydrofuran / 32 h / 60 °C / Inert atmosphere

15.1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere

16.1: caesium carbonate / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere

17.1: dmap; triethylamine / dichloromethane / 0.25 h / 23 °C / Inert atmosphere

18.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tetrahydrofuran; water; tert-butyl alcohol / 18 h / 23 °C / Inert atmosphere

19.1: methanol; tetrahydrofuran / 0.25 h / 23 °C / Inert atmosphere

20.1: ethanol / 7 h / 55 °C / Inert atmosphere

With triethylsilane; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; (trimethylphosphine)gold(I) chloride; ethanol; silver trifluoromethanesulfonate; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; toluene; acetonitrile; tert-butyl alcohol; benzene; 2.3: |Wittig Olefination / 8.1: |Fischer Indole Synthesis;

DOI:10.1021/jacs.8b03404

Reference yield:

C36H44N2O6SSi → akuammiline (1897-26-3)

Guidance literature:

Multi-step reaction with 19 steps

1.1: toluene-4-sulfonic acid / water / Inert atmosphere

1.2: 65 °C / Inert atmosphere

1.3: -78 - 23 °C / Inert atmosphere

2.1: potassium carbonate; N-iodo-succinimide / 23 °C / Inert atmosphere

3.1: acetic acid / water; tetrahydrofuran / 75 °C / Inert atmosphere

4.1: sodium tetrahydroborate / methanol / 0 °C / Inert atmosphere

5.1: toluene-4-sulfonic acid / benzene / 80 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 40 °C / Inert atmosphere

7.1: trifluoroacetic acid / 1,2-dichloro-ethane / 12 h / 40 °C / Inert atmosphere

8.1: trifluoroacetic acid; triethylsilane / 1,2-dichloro-ethane / 1 h / 23 °C / Inert atmosphere

9.1: sodium hydroxide / tetrahydrofuran; water / 14 h / 23 °C / Inert atmosphere

10.1: dichloromethane; hexane / 0.5 h / 23 °C / Inert atmosphere

11.1: dmap; triethylamine / dichloromethane / 2 h / 23 °C / Inert atmosphere

12.1: caesium carbonate / acetonitrile / 46 h / 40 °C / Inert atmosphere

13.1: tetrahydrofuran / 32 h / 60 °C / Inert atmosphere

14.1: pyridinium chlorochromate / dichloromethane / 2 h / 23 °C / Inert atmosphere

15.1: caesium carbonate / tetrahydrofuran / 12 h / 23 °C / Inert atmosphere

16.1: dmap; triethylamine / dichloromethane / 0.25 h / 23 °C / Inert atmosphere

17.1: 2-methyl-but-2-ene; sodium dihydrogenphosphate; sodium chlorite / tetrahydrofuran; water; tert-butyl alcohol / 18 h / 23 °C / Inert atmosphere

18.1: methanol; tetrahydrofuran / 0.25 h / 23 °C / Inert atmosphere

19.1: ethanol / 7 h / 55 °C / Inert atmosphere

With triethylsilane; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; 2-methyl-but-2-ene; ethanol; potassium carbonate; caesium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol; benzene; 1.3: |Wittig Olefination / 7.1: |Fischer Indole Synthesis;

DOI:10.1021/jacs.8b03404

upstream raw materials:

acetic anhydride

(E)-(16R)-17-hydroxy-16-(methoxycarbonyl)-1,2-dehydro-curan-18-ene

Refernces

Macroline, akuammiline, sarpagine, and ajmaline alkaloids from Alstonia macrophylla

10.1016/j.phytochem.2013.11.014

Siew-Huah Lim et al. detail the isolation and structural determination of 17 new indole alkaloids from the stem-bark and leaf extracts of the Malayan Alstonia macrophylla. These alkaloids, which include macroline, sarpagine, akuammiline, and ajmaline types, were identified using NMR, MS, and X-ray diffraction analysis. Six of these alkaloids demonstrated the ability to reverse multidrug resistance (MDR) in vincristine-resistant KB cells. The study highlights the chemical diversity of Alstonia macrophylla and its potential for yielding compounds with significant biological activities, particularly in the context of overcoming drug resistance in cancer therapy.

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