(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol

Base Information

• Chemical Name: (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol
• CAS No.: 149400-38-4
• Molecular Formula: C₃₈H₅₆O₅Si
• Molecular Weight: 620.945
• Mol file: 149400-38-4.mol

Synonyms:

Chemical Property of (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol

There total 8 articles about (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-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) → (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol (149400-38-4,149400-39-5)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; lithium perchlorate; diisobutylaluminium hydride; diborane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

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) → (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol (149400-38-4,149400-39-5)

Guidance literature:

Multi-step reaction with 6 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; lithium perchlorate; diisobutylaluminium hydride; diborane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

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) → (3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-hexadecahydro-6-oxa-benzo[de]anthracen-2-ol (149400-38-4,149400-39-5)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; hydrogenchloride; sodium hydroxide; dihydrogen peroxide; diisobutylaluminium hydride; diborane; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ja00181a079

upstream raw materials:

tert-Butyl-((3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-5,11-dimethoxy-3,8,11a-trimethyl-1,4,5,6a,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:

(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-2-one

(3R,3aS,5S,6aR,7aS,8R,11R,11aS,11bR,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-5,11-dimethoxy-3,8,11a-trimethyl-tetradecahydro-6-oxa-benzo[de]anthracen-2-one

(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

C₄₅H₆₂N₂O₆SSi