(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

Base Information

• Chemical Name: (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one
• CAS No.: 866430-88-8
• Molecular Formula: C₃₆H₅₄O₄Si₂
• Molecular Weight: 606.993
• Mol file: 866430-88-8.mol

Synonyms:(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

Chemical Property of (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one

There total 7 articles about (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-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: 77.0%

(Z)-(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,11,12,12a-octahydro-7-oxa-benzocyclodecen-6-one (866430-87-7) → (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one (866430-88-8)

Guidance literature:

With hydrogen; Wilkinson's catalyst; for 45h; under 760 Torr;

DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

[(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester (866430-81-1) → (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one (866430-88-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

2: 83 percent / Ti(OiPr)4 / 10 h / 90 °C

3: 30 percent / Ti(OiPr)4 / (PCy₃)2(Cl)2Ru=CHPh / benzene / 2 h / 80 °C

4: 77 percent / H₂ / (Ph₃P)3RhCl / 45 h / 760 Torr

With 1H-imidazole; titanium(IV) isopropylate; hydrogen; Wilkinson's catalyst; Grubbs catalyst first generation; In N,N-dimethyl-formamide; benzene;

DOI:10.1016/j.tetlet.2005.07.152

Reference yield:

[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester (866430-79-7) → (1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one (866430-88-8)

Guidance literature:

Multi-step reaction with 5 steps

1: NaBH₄; CeCl₃ / methanol / -50 °C

2: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

3: 83 percent / Ti(OiPr)4 / 10 h / 90 °C

4: 30 percent / Ti(OiPr)4 / (PCy₃)2(Cl)2Ru=CHPh / benzene / 2 h / 80 °C

5: 77 percent / H₂ / (Ph₃P)3RhCl / 45 h / 760 Torr

With 1H-imidazole; titanium(IV) isopropylate; sodium tetrahydroborate; cerium(III) chloride; hydrogen; Wilkinson's catalyst; Grubbs catalyst first generation; In methanol; N,N-dimethyl-formamide; benzene; 1: Luche reduction;

DOI:10.1016/j.tetlet.2005.07.152

upstream raw materials:

(Z)-(1R,4S,4aR,8R,12aR)-1-(tert-Butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-8-methyl-1,4,4a,5,8,11,12,12a-octahydro-7-oxa-benzocyclodecen-6-one

[(1R,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-cyclohex-3-enyl]-acetic acid ethyl ester

[(1R,2S,5R,6R)-6-But-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-cyclohex-3-enyl]-acetic acid ethyl ester

[6-but-3-enyl-5-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-diphenyl-silanyloxy)-cyclohex-3-enyl]-acetic acid ethyl ester

Downstream raw materials:

(4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-8-methyl-4a,5,8,9,10,11,12,12a-octahydro-4H-7-oxa-benzocyclodecene-1,6-dione

(1R,4S,4aR,8R,12aR)-4-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxy-8-methyl-1,4,4a,5,8,9,10,11,12,12a-decahydro-7-oxa-benzocyclodecen-6-one