ProtosteMotinine

Base Information

• Chemical Name: ProtosteMotinine
• CAS No.: 169534-85-4
• Molecular Formula: C23H29NO6
• Molecular Weight: 415.47900
• Mol file: 169534-85-4.mol

Synonyms:(3S,11S,11aS)-3'-Methoxy-4',9-dimethyl-3-[(2S,4S)-4-methyl-5-oxotetrahydrofuran-2-yl]-2,3,5,6,7,8-hexahydro-1H,5'H,10H-spiro[cyclopenta[b]pyrrolo[1,2-a]azepine-11,2'-furan]-5',10-dione; spiro[1H-cyclopenta[b]pyrrolo[1,2-a]azepine-11(10H),2'(5'H)-furan]-5',10-dione, 2,3,5,6,7,8-hexahydro-3'-methoxy-4',9-dimethyl-3-[(2S,4S)-tetrahydro-4-methyl-5-oxo-2-furanyl]-, (3S,11S,11aS)-

Chemical Property of ProtosteMotinine

Chemical Property:

• PSA: 82.14000
• Density: 1.31±0.1 g/cm3 (20 oC 760 Torr)
• LogP: 2.37820

Purity/Quality:

98%,99%, ^*data from raw suppliers

Protostemotinine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ProtosteMotinine

There total 21 articles about ProtosteMotinine 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: 66.0%

C19H23NO5 + ethyl 2-bromomethyl-2-propenoate (17435-72-2) → (+/-)-maistemonine (169534-85-4)

Guidance literature:

C₁₉H₂₃NO₅; With zinc; In tetrahydrofuran; Inert atmosphere; Heating;

ethyl 2-bromomethyl-2-propenoate; In tetrahydrofuran; for 0.166667h; Inert atmosphere; Reflux;

With palladium 10% on activated carbon; hydrogen; In ethanol; for 15h; under 760.051 Torr; stereoselective reaction;

DOI:10.1039/c0cc02612c

Reference yield:

C14H20O3 (1146158-59-9) → (+/-)-maistemonine (169534-85-4)

Guidance literature:

Multi-step reaction with 14 steps

1.1: tetrahydrofuran / 7.5 h / -78 °C / Inert atmosphere

2.1: pyridine; dmap / 0.5 h / 40 °C / Inert atmosphere

3.1: sodium azide / N,N-dimethyl-formamide / 1.5 h / 40 °C / Inert atmosphere

4.1: titanium tetrachloride / dichloromethane / 0.33 h / -15 °C / Inert atmosphere

5.1: ozone / dichloromethane / 11 h / -78 °C

6.1: quinoline; 5% Pd-CaCO3; hydrogen / dichloromethane / 1.5 h / 20 °C

7.1: potassium carbonate / methanol / 1 h / 20 °C

8.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

8.2: 1 h / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

9.2: 20 h / 20 °C / 225.02 Torr

10.1: dmap; triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

11.1: potassium hexamethylsilazane / tetrahydrofuran / 5 h / -78 - 10 °C / Inert atmosphere

11.2: 1 h / 0 °C / Inert atmosphere

12.1: methyl trifluoromethanesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere

12.2: 0.17 h / 20 °C

13.1: potassium osmate(VI); 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 3.5 h / 20 °C

13.2: 3 h / 0 °C / Inert atmosphere

14.1: zinc / tetrahydrofuran / Inert atmosphere; Heating

14.2: 0.17 h / Inert atmosphere; Reflux

14.3: 15 h / 760.05 Torr

With pyridine; quinoline; dmap; potassium osmate(VI); sodium azide; 5% Pd-CaCO3; hydrogen; titanium tetrachloride; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; triethylamine; methyl trifluoromethanesulfonate; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; 1.1: Grignard reaction / 4.1: Schmidt reaction / 6.1: Lindlar reduction / 7.1: Aldol condensation / 14.1: Reformatsky reaction / 14.2: Reformatsky reaction;

DOI:10.1039/c0cc02612c

Reference yield:

C16H21NO2 → (+/-)-maistemonine (169534-85-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: ozone / dichloromethane / 11 h / -78 °C

2.1: quinoline; 5% Pd-CaCO3; hydrogen / dichloromethane / 1.5 h / 20 °C

3.1: potassium carbonate / methanol / 1 h / 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

4.2: 1 h / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

5.2: 20 h / 20 °C / 225.02 Torr

6.1: dmap; triethylamine / dichloromethane / 24 h / 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran / 5 h / -78 - 10 °C / Inert atmosphere

7.2: 1 h / 0 °C / Inert atmosphere

8.1: methyl trifluoromethanesulfonate / dichloromethane / 12 h / 20 °C / Inert atmosphere

8.2: 0.17 h / 20 °C

9.1: potassium osmate(VI); 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 3.5 h / 20 °C

9.2: 3 h / 0 °C / Inert atmosphere

10.1: zinc / tetrahydrofuran / Inert atmosphere; Heating

10.2: 0.17 h / Inert atmosphere; Reflux

10.3: 15 h / 760.05 Torr

With quinoline; dmap; potassium osmate(VI); 5% Pd-CaCO3; hydrogen; potassium hexamethylsilazane; potassium carbonate; Dess-Martin periodane; ozone; 4-methylmorpholine N-oxide; triethylamine; methyl trifluoromethanesulfonate; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; methanol; dichloromethane; water; acetone; tert-butyl alcohol; 2.1: Lindlar reduction / 3.1: Aldol condensation / 10.1: Reformatsky reaction / 10.2: Reformatsky reaction;

DOI:10.1039/c0cc02612c

upstream raw materials:

C₁₄H₂₀O₃

ethyl 2-bromomethyl-2-propenoate

C₁₇H₂₄O₅S

Refernces

• 1、 Chen, Zhi-Hua,Chen, Zhi-Min,Zhang, Yong-Qiang,Tu, Yong-Qiang,Zhang, Fu-Min. "Total synthesis of (±)-maistemonine, (±)-stemonamide, and (±)-isomaistemonine". . p. 10173 - 10186. Retrieved 2012/02/05.