(3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol

Base Information

• Chemical Name: (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol
• CAS No.: 130146-59-7
• Molecular Formula: C₃₇H₅₂O₄Si
• Molecular Weight: 588.903
• Mol file: 130146-59-7.mol

Synonyms:

Chemical Property of (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol

There total 15 articles about (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol 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) → (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol (130146-59-7,149400-18-0,149400-43-1)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; hydrogenchloride; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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) → (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol (130146-59-7,149400-18-0,149400-43-1)

Guidance literature:

Multi-step reaction with 13 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

With 1H-imidazole; hydrogenchloride; palladium diacetate; sodium hydroxide; sodium tetrahydroborate; n-butyllithium; ammonia; dihydrogen peroxide; sodium acetate; lithium perchlorate; lithium; diisobutylaluminium hydride; sodium carbonate; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 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) → (3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5-methoxy-3,8,11a-trimethyl-3,3a,4,5,6a,7,7a,8,9,10,11,11a,11b,11c-tetradecahydro-6-oxa-benzo[de]anthracen-11-ol (130146-59-7,149400-18-0,149400-43-1)

Guidance literature:

Multi-step reaction with 11 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

With 1H-imidazole; hydrogenchloride; palladium diacetate; sodium hydroxide; n-butyllithium; ammonia; dihydrogen peroxide; sodium acetate; lithium; diisobutylaluminium hydride; sodium carbonate; pyridinium chlorochromate; diborane; tert-butyl alcohol; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/ja00181a079

upstream raw materials:

tert-Butyl-((3S,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-5,11-dimethoxy-3,8,11a-trimethyl-3,4,5,6a,7,7a,8,9,10,11,11a,11b-dodecahydro-3aH-6-oxa-benzo[de]anthracen-11c-ylmethoxy)-diphenyl-silane

(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:

(+/-)-chaparrinone

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

Acetic acid (1R,2S,3S,3aR,5R,6aS,7aR,8S,11S,11aR,11bS,11cR)-11c-(tert-butyl-diphenyl-silanyloxymethyl)-1,11-dihydroxy-5-methoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-yl ester

(2S,3S,3aR,5R,6aS,7aR,8S,11aR,11bR,11cR)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-2-hydroxy-5-methoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracene-1,11-dione