(2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione

Base Information

• Chemical Name: (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione
• CAS No.: 149400-25-9
• Molecular Formula: C₃₉H₅₀O₈Si
• Molecular Weight: 674.907
• Mol file: 149400-25-9.mol

Synonyms:(2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione

Chemical Property of (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione

There total 40 articles about (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione 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:

(2R,3R,3aS,6aR,7aS,8S,11S,11aS,11bR,11cS)-9-Bromo-11c-(tert-butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione (149400-46-4) → (+)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1-methoxy-12-(methoxymethoxy)picras-3-ene-2,11,16-trione (149400-25-9)

Guidance literature:

With lithium carbonate; lithium bromide; In N,N-dimethyl-formamide; at 120 ℃; for 1h; Yield given;

DOI:10.1021/ja00067a025

Reference yield:

(E)-4-methyl-3,5-hexadienoic acid (95421-98-0) → (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione (149400-25-9)

Guidance literature:

Multi-step reaction with 22 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

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; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; 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) → (2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione (149400-25-9)

Guidance literature:

Multi-step reaction with 22 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

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; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; 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

upstream raw materials:

(2S,3S,3aR,6aS,7aR,8S,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-11-methoxy-2-methoxymethoxy-3,8,11a-trimethyl-dodecahydro-6-oxa-benzo[de]anthracene-1,5,10-trione

(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

(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

Downstream raw materials:

(2S,3S,3aR,6aS,7aR,11R,11aR,11bS,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2,11-dihydroxy-3,8,11a-trimethyl-2,3,3a,4,7,7a,11,11a,11b,11c-decahydro-6aH-6-oxa-benzo[de]anthracene-1,5,10-trione

chaparrinone

(+)-(1β,12α)-20-(tert-butyldiphenylsiloxy)-1,12-dihydroxypicras-3-ene-2,11,16-trione

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