(2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester

Base Information

• Chemical Name: (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester
• CAS No.: 184299-64-7
• Molecular Formula: C₃₂H₄₂O₈
• Molecular Weight: 554.681

Synonyms:

Chemical Property of (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester

There total 16 articles about (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-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:

(E)-(2S,3R)-3-Hydroxy-2,4-dimethyl-hex-4-enoic acid methyl ester (1197011-35-0) → (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester (184299-64-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 1M aq. LiOH / methanol

2: Ph₃P, DEAD / tetrahydrofuran

3: imidazole / dimethylformamide

4: NBS / CCl₄ / 80 °C

5: Ag₂CO₃ / dimethylsulfoxide / 0.33 h / 90 °C

6: 66 percent / LiN(TMS)2 / tetrahydrofuran

7: 67 percent / TBAF / tetrahydrofuran / 1 h

8: Et₃N / tetrahydrofuran / 0.5 h

9: DMAP / toluene / 2 h

10: TBAF / tetrahydrofuran / 2 h

11: 0.1M NaOH / dioxane / 0.5 h

12: 5percent H₃PO₄ / dioxane / 2 h

13: ethanol

With 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; phosphoric acid; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; silver carbonate; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(96)02377-5

Reference yield:

(-)-(2S,3R)-methyl 3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (187038-21-7) → (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester (184299-64-7)

Guidance literature:

Multi-step reaction with 14 steps

1: K₂CO₃ / methanol

2: 1M aq. LiOH / methanol

3: Ph₃P, DEAD / tetrahydrofuran

4: imidazole / dimethylformamide

5: NBS / CCl₄ / 80 °C

6: Ag₂CO₃ / dimethylsulfoxide / 0.33 h / 90 °C

7: 66 percent / LiN(TMS)2 / tetrahydrofuran

8: 67 percent / TBAF / tetrahydrofuran / 1 h

9: Et₃N / tetrahydrofuran / 0.5 h

10: DMAP / toluene / 2 h

11: TBAF / tetrahydrofuran / 2 h

12: 0.1M NaOH / dioxane / 0.5 h

13: 5percent H₃PO₄ / dioxane / 2 h

14: ethanol

With 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; phosphoric acid; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; triphenylphosphine; silver carbonate; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(96)02377-5

Reference yield:

(+/-)-methyl 3-acetoxy-2,4-dimethyl-hex-(4E)-enoate (107184-58-7,107184-61-2,107243-50-5,107243-53-8) → (2E,4E,6E,8E)-(10R,11S)-10-Hydroxy-5,9,11-trimethyl-dodeca-2,4,6,8-tetraenedioic acid 12-((3R,4aR,8S,10S,10aS,10bR)-3-hydroxy-4a,8,10b-trimethyl-1-oxo-2,3,4a,8,9,10,10a,10b-octahydro-1H-benzo[f]chromen-10-yl) ester 1-methyl ester (184299-64-7)

Guidance literature:

Multi-step reaction with 15 steps

1: lipase Amano A-6 / 120 h / 33 °C / phosphate buffer

2: K₂CO₃ / methanol

3: 1M aq. LiOH / methanol

4: Ph₃P, DEAD / tetrahydrofuran

5: imidazole / dimethylformamide

6: NBS / CCl₄ / 80 °C

7: Ag₂CO₃ / dimethylsulfoxide / 0.33 h / 90 °C

8: 66 percent / LiN(TMS)2 / tetrahydrofuran

9: 67 percent / TBAF / tetrahydrofuran / 1 h

10: Et₃N / tetrahydrofuran / 0.5 h

11: DMAP / toluene / 2 h

12: TBAF / tetrahydrofuran / 2 h

13: 0.1M NaOH / dioxane / 0.5 h

14: 5percent H₃PO₄ / dioxane / 2 h

15: ethanol

With 1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; phosphoric acid; lipase Amano A-6; tetrabutyl ammonium fluoride; potassium carbonate; triethylamine; triphenylphosphine; silver carbonate; lithium hexamethyldisilazane; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; methanol; tetrachloromethane; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4039(96)02377-5

upstream raw materials:

calbistrin A

diazomethyl-trimethyl-silane

(E)-(2S,3R)-3-Hydroxy-2,4-dimethyl-hex-4-enoic acid methyl ester

(-)-(2S,3R)-methyl 3-acetoxy-2,4-dimethyl-hex-(4E)-enoate

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