(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

Base Information

Chemical Name:(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol
CAS No.:201670-64-6
Molecular Formula:C₅₁H₇₆O₂Si
Molecular Weight:749.249
Hs Code.:

(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

Synonyms:(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

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Chemical Property of (2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

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Technology Process of (2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

There total 16 articles about (2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-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: 84.0%

: 201670-63-5
(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trienoic acid methyl ester

: 201670-64-6
(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

Guidance literature:: With diisobutylaluminium hydride; In toluene; at -78 ℃; for 0.5h;
DOI:10.1016/S0040-4020(97)10260-5

Reference yield:

: 106-25-2
Nerol

: 201670-64-6
(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

Guidance literature:: Multi-step reaction with 12 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

With pyridine; 1H-imidazole; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 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:

: 139109-03-8
(Z)-1-[(tert-butyldiphenylsilyl)oxy]-3,7-dimethyl-2,6-octadiene

: 201670-64-6
(2E,6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-6,10-dimethyl-2-[2-((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)-ethyl]-dodeca-2,6,10-trien-1-ol

Guidance literature:: Multi-step reaction with 11 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

With pyridine; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;
DOI:10.1016/S0040-4020(97)10260-5