2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate

Base Information

• Chemical Name: 2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate
• CAS No.: 990-33-0
• Molecular Formula: C₂₆H₃₂O₁₀
• Molecular Weight: 504.534

Synonyms:

Chemical Property of 2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate

Chemical Property:

• Vapor Pressure: 5.85E-16mmHg at 25°C
• Boiling Point: 633.6°Cat760mmHg
• Flash Point: 269.3°C
• Density: 1.31g/cm³

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate

There total 28 articles about 2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate 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)-4-methyl-3,5-hexadienoic acid (95421-98-0) → Acetic acid (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-2,11-diacetoxy-3,8,11a-trimethyl-1,5,10-trioxo-1,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-2H-6-oxa-benzo[de]anthracen-11c-ylmethyl ester (751-66-6,990-33-0)

Guidance literature:

Multi-step reaction with 25 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

20: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF

21: 1.) HCl, 2.) PCC, NaOAc / 1.) H₂O, THF, 2.) CH₂Cl₂

22: 1.) PyHBr₃, CSA, 2.) LiBr, Li₂CO₃ / 1.) THF, 1 h, 2.) DMF, 120 deg C, 1 h

23: BBr₃ / CH₂Cl₂ / 1.5 h / -78 - -23 °C

24: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

25: pyridine, DMAP

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; boron tribromide; lithium; lithium carbonate; diisobutylaluminium hydride; sodium carbonate; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

Reference yield:

(4aR,5S,8S,8aR)-8-Methoxy-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde (86669-09-2,87758-23-4,123929-85-1) → Acetic acid (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-2,11-diacetoxy-3,8,11a-trimethyl-1,5,10-trioxo-1,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-2H-6-oxa-benzo[de]anthracen-11c-ylmethyl ester (751-66-6,990-33-0)

Guidance literature:

Multi-step reaction with 25 steps

1: 72 percent / LiClO₄ / diethyl ether / 9 h / Ambient temperature

2: 1.) NaBH₄, 2.) concd. HCl / 1.) methanol, 0 deg C

3: 86 percent / imidazole / dimethylformamide

4: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

5: 100 percent / concd. HCl / tetrahydrofuran

6: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

7: PCC, NaOAc / CH₂Cl₂

8: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

9: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

10: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

11: methanol; tetrahydrofuran

12: n-butyllithium / -78 °C

14: 100 percent / Et₃N, DMAP / CH₂Cl₂

15: 83 percent / OsO₄, pyridine

16: Collins reagent

17: NaOH / methanol; tetrahydrofuran

18: i-Pr₂NEt / 1,2-dichloro-ethane

19: 1.) LiHMDS, HMPA / tetrahydrofuran

20: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF

21: 1.) HCl, 2.) PCC, NaOAc / 1.) H₂O, THF, 2.) CH₂Cl₂

22: 1.) PyHBr₃, CSA, 2.) LiBr, Li₂CO₃ / 1.) THF, 1 h, 2.) DMF, 120 deg C, 1 h

23: BBr₃ / CH₂Cl₂ / 1.5 h / -78 - -23 °C

24: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

25: pyridine, DMAP

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; boron tribromide; lithium; lithium carbonate; diisobutylaluminium hydride; sodium carbonate; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

Reference yield:

(3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-Hydroxymethyl-11-methoxy-3,8,11a-trimethyl-3a,4,6a,7,7a,8,9,10,11,11a,11b,11c-dodecahydro-1H-6-oxa-benzo[de]anthracen-5-one (125458-63-1,149400-06-6) → Acetic acid (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-2,11-diacetoxy-3,8,11a-trimethyl-1,5,10-trioxo-1,3,3a,4,5,6a,7,7a,10,11,11a,11b-dodecahydro-2H-6-oxa-benzo[de]anthracen-11c-ylmethyl ester (751-66-6,990-33-0)

Guidance literature:

Multi-step reaction with 23 steps

1: 86 percent / imidazole / dimethylformamide

2: 100 percent / i-Bu₂AlH / tetrahydrofuran / -78 °C

3: 100 percent / concd. HCl / tetrahydrofuran

4: 1.) B₂H₆, 2.) 3 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C

5: PCC, NaOAc / CH₂Cl₂

6: 1.) LDA / 1.) THF, from -78 deg C to 0 deg C, 2.) -78 deg C

7: Pd(OAc)2, Na₂CO₃ / acetonitrile / 45 °C

8: 81 percent / lithium, liquid ammonia, tert-butyl alcohol / -78 °C

9: methanol; tetrahydrofuran

10: n-butyllithium / -78 °C

12: 100 percent / Et₃N, DMAP / CH₂Cl₂

13: 83 percent / OsO₄, pyridine

14: Collins reagent

15: NaOH / methanol; tetrahydrofuran

16: i-Pr₂NEt / 1,2-dichloro-ethane

17: 1.) LiHMDS, HMPA / tetrahydrofuran

18: 1.) B₂H₆, 2.) NaOH, H₂O₂ / 1.) THF

19: 1.) HCl, 2.) PCC, NaOAc / 1.) H₂O, THF, 2.) CH₂Cl₂

20: 1.) PyHBr₃, CSA, 2.) LiBr, Li₂CO₃ / 1.) THF, 1 h, 2.) DMF, 120 deg C, 1 h

21: BBr₃ / CH₂Cl₂ / 1.5 h / -78 - -23 °C

22: tetra-n-butylammonium fluoride / tetrahydrofuran / 0.5 h

23: pyridine, DMAP

With pyridine; 1H-imidazole; hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; palladium diacetate; sodium hydroxide; osmium(VIII) oxide; n-butyllithium; Collins oxidation agent; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; ammonia; dihydrogen peroxide; sodium acetate; boron tribromide; lithium; lithium carbonate; diisobutylaluminium hydride; sodium carbonate; pyridinium hydrobromide perbromide; triethylamine; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; lithium bromide; diborane; lithium hexamethyldisilazane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

upstream raw materials:

shinjulactone G

acetic anhydride

(+/-)-chaparrinone

(E)-4-methyl-3,5-hexadienoic acid

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 990-33-0 2,11,16-trioxopicras-3-ene-1,12,20-triyl triacetate

Send

Send

Metric Ton KG G Pound L ML

Send

Send