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

Base Information

• Chemical Name: 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
• CAS No.: 751-66-6
• Molecular Formula: C₂₆H₃₂O₁₀
• Molecular Weight: 504.534
• Mol file: 751-66-6.mol

Synonyms:

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 26 articles about 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 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:

acetic anhydride

(+/-)-chaparrinone

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

(4aR,5S,8S,8aR)-8-Methoxy-5,8a-dimethyl-3-oxo-3,4,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde