(3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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

Base Information

• Chemical Name: (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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
• CAS No.: 130575-32-5
• Molecular Formula: C₃₇H₅₀O₄Si
• Molecular Weight: 586.887

Synonyms:

Chemical Property of (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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

There total 4 articles about (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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 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: 86.0%

(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) + tert-butylchlorodiphenylsilane (58479-61-1) → (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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 (130575-32-5,149400-09-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1021/ja00181a079

Reference yield:

(E)-4-methyl-3,5-hexadienoic acid (95421-98-0) → (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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 (130575-32-5,149400-09-9)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium perchlorate; In 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) → (3aS,6aR,7aS,8R,11R,11aS,11bS,11cS)-11c-(tert-Butyl-diphenyl-silanyloxymethyl)-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 (130575-32-5,149400-09-9)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; lithium perchlorate; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/ja00181a079

upstream raw materials:

(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

tert-butylchlorodiphenylsilane

(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

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

(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

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

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