(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

Base Information

Chemical Name:(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester
CAS No.:201670-62-4
Molecular Formula:C₅₂H₇₈O₄Si
Molecular Weight:795.274
Hs Code.:

(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

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Chemical Property of (6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

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Technology Process of (6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

There total 13 articles about (6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester 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: 35.0%

: 139108-85-3
isocopalenyl iodide

: 201670-60-2
(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-6,10-dimethyl-2-methylene-dodeca-6,10-dienoic acid methyl ester

: 201670-62-4
(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

Guidance literature:: With tri-n-butyl-tin hydride; In diethyl ether; for 6h; Irradiation;
DOI:10.1016/S0040-4020(97)10260-5

Reference yield:

: 106-25-2
Nerol

: 201670-62-4
(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

With pyridine; 1H-imidazole; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; 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

: 201670-62-4
(6Z,10Z)-12-(tert-Butyl-diphenyl-silanyloxy)-3-hydroxy-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-6,10-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

With pyridine; 18-crown-6 ether; dimethylsulfide; tri-n-butyl-tin hydride; phosphorus tribromide; potassium hexamethylsilazane; diisobutylaluminium hydride; ozone; 3-quinuclidinol; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; toluene;
DOI:10.1016/S0040-4020(97)10260-5