tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane

Base Information

• Chemical Name: tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane
• CAS No.: 201670-65-7
• Molecular Formula: C₅₁H₇₆OSi
• Molecular Weight: 733.249

Synonyms:

Chemical Property of tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane

There total 18 articles about tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane 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:

Nerol (106-25-2) → tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane (201670-65-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / imidazole / dimethylformamide / 0.25 h / Ambient temperature

2: 1) O₃, pyridine, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C -> room temperature, 2 h

3: 63 percent / KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

4: 59 percent / DIBAH / toluene; tetrahydrofuran / 0.25 h / -78 °C

5: PBr₃ / diethyl ether / 1.5 h / Ambient temperature

6: 2.14 g / LiN(i-Pr)2 / tetrahydrofuran / 0.33 h / -78 °C

7: 85 percent / DIBAH / toluene / 0.08 h / 0 °C

8: 50 percent / quinuclidin-3-ol / 144 h / Ambient temperature

9: 35 percent / n-Bu₃SnH / diethyl ether / 6 h / Irradiation

10: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

11: 37 mg / DBU / toluene / 4 h / Heating

12: 84 percent / DIBAH / toluene / 0.5 h / -78 °C

13: PPh₃, CCl₄ / 72 h / Heating

14: 18 mg / LiBHEt₃ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; tetrachloromethane; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(97)10260-5

Reference yield:

(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene (139109-03-8) → tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane (201670-65-7)

Guidance literature:

Multi-step reaction with 13 steps

1: 1) O₃, pyridine, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C -> room temperature, 2 h

2: 63 percent / KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

3: 59 percent / DIBAH / toluene; tetrahydrofuran / 0.25 h / -78 °C

4: PBr₃ / diethyl ether / 1.5 h / Ambient temperature

5: 2.14 g / LiN(i-Pr)2 / tetrahydrofuran / 0.33 h / -78 °C

6: 85 percent / DIBAH / toluene / 0.08 h / 0 °C

7: 50 percent / quinuclidin-3-ol / 144 h / Ambient temperature

8: 35 percent / n-Bu₃SnH / diethyl ether / 6 h / Irradiation

9: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

10: 37 mg / DBU / toluene / 4 h / Heating

11: 84 percent / DIBAH / toluene / 0.5 h / -78 °C

12: PPh₃, CCl₄ / 72 h / Heating

13: 18 mg / LiBHEt₃ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; tetrachloromethane; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0040-4020(97)10260-5

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → tert-Butyl-diphenyl-[(2Z,6Z,10Z)-3,7,11-trimethyl-13-((1S,4aS,4bR,8aR,10aR)-2,4b,8,8,10a-pentamethyl-1,4,4a,4b,5,6,7,8,8a,9,10,10a-dodecahydro-phenanthren-1-yl)-trideca-2,6,10-trienyloxy]-silane (201670-65-7)

Guidance literature:

Multi-step reaction with 14 steps

1: 100 percent / imidazole / dimethylformamide / 0.25 h / Ambient temperature

2: 1) O₃, pyridine, 2) Me₂S / 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C -> room temperature, 2 h

3: 63 percent / KN(SiMe₃)2, 18-crown-6 / tetrahydrofuran / 1 h / -78 °C

4: 59 percent / DIBAH / toluene; tetrahydrofuran / 0.25 h / -78 °C

5: PBr₃ / diethyl ether / 1.5 h / Ambient temperature

6: 2.14 g / LiN(i-Pr)2 / tetrahydrofuran / 0.33 h / -78 °C

7: 85 percent / DIBAH / toluene / 0.08 h / 0 °C

8: 50 percent / quinuclidin-3-ol / 144 h / Ambient temperature

9: 35 percent / n-Bu₃SnH / diethyl ether / 6 h / Irradiation

10: Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

11: 37 mg / DBU / toluene / 4 h / Heating

12: 84 percent / DIBAH / toluene / 0.5 h / -78 °C

13: PPh₃, CCl₄ / 72 h / Heating

14: 18 mg / LiBHEt₃ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 1H-imidazole; tetrachloromethane; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; lithium triethylborohydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; triphenylphosphine; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0040-4020(97)10260-5

upstream raw materials:

Nerol

(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3-methyl-2-hexen-6-al

(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene

(Z)-1-(tert-butyldiphenylsilyloxy)-6,7-epoxy-3,7-dimethylocta-2-ene

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