1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

Base Information

Chemical Name:1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol
CAS No.:758719-37-8
Molecular Formula:C₄₇H₇₂O₄Si
Molecular Weight:729.172
Hs Code.:

1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

Synonyms:1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

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Chemical Property of 1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

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Technology Process of 1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

There total 16 articles about 1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol 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: 48.0%

: 758719-49-2
(1S,3R,4R,5S)-3-(tert-butyldiphenylsilyloxy)-4-methylbicyclo[3.1.0]hexane-1-carbaldehyde

: (1R,3aR,7aR)-4-[1-Bromo-meth-(E)-ylidene]-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-indene

: 758719-37-8
1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

Guidance literature:: With tert.-butyl lithium; In tetrahydrofuran; at -78 - -10 ℃; for 2.5h;
DOI:10.1002/ejoc.200500289

Reference yield:

: 757240-15-6
(1R,5R)-5-Hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

: 758719-37-8
1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 1.68 g / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

2.1: BH₃ / tetrahydrofuran / 2.5 h / 0 °C

2.2: 35 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

3.1: 81 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

4.1: 95 percent / K₂CO₃ / methanol / 6 h / 20 °C

5.1: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

6.1: 71 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

7.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

8.1: NMO; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 48 percent / tBuLi / tetrahydrofuran / 2.5 h / -78 - -10 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-isopropyl azodicarboxylate; borane; potassium tert-butylate; tert.-butyl lithium; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Mitsunobu inversion;
DOI:10.1002/ejoc.200500289

Reference yield:

: 326622-28-0
(4R,6R)-6-acetoxy-1-methyl-4-(methoxycarbonyl)cyclohexene

: 758719-37-8
1-[(1S,3R,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-bicyclo[3.1.0]hex-1-yl]-2-[(1R,3aS,7aR)-1-[(R)-5-(1-ethoxy-ethoxy)-1,5-dimethyl-hexyl]-7a-methyl-octahydro-inden-(4E)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 10 steps

1.1: K₂CO₃ / methanol / 6 h

2.1: 1.68 g / imidazole; DMAP / dimethylformamide / 10 h / 20 °C

3.1: BH₃ / tetrahydrofuran / 2.5 h / 0 °C

3.2: 35 percent / H₂O₂; NaHCO₃ / tetrahydrofuran / 0.5 h

4.1: 81 percent / PPh₃; DIAD / tetrahydrofuran / 24 h / 20 °C

5.1: 95 percent / K₂CO₃ / methanol / 6 h / 20 °C

6.1: 94 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

7.1: 71 percent / tBuOK / tetrahydrofuran; 2-methyl-propan-2-ol / 0.5 h / 45 - 50 °C

8.1: LiAlH₄ / tetrahydrofuran / 1.5 h / 0 °C

9.1: NMO; TPAP / CH₂Cl₂ / 0.5 h / 20 °C

10.1: 48 percent / tBuLi / tetrahydrofuran / 2.5 h / -78 - -10 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; di-isopropyl azodicarboxylate; borane; potassium tert-butylate; tert.-butyl lithium; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 4.1: Mitsunobu inversion;
DOI:10.1002/ejoc.200500289