(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

Base Information

Chemical Name:(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester
CAS No.:928621-28-7
Molecular Formula:C₅₅H₉₄O₇Si₄
Molecular Weight:979.689
Hs Code.:

(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

Synonyms:(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

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Chemical Property of (2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

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Technology Process of (2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

There total 11 articles about (2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic 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:

: 936015-51-9
(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,17-bis-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13,15-dihydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 928621-28-7
(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

: (2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,13,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-15-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 23 ℃; for 18h;
DOI:10.1021/ol0629869

Reference yield:

: 928621-18-5
(3R,4S)-1-(tert-butyl-diphenyl-silanyloxy)-4-(4,4,5,5-tetraphenyl-[1,3,2]dioxaborolan-2-yl)hex-5-en-3-ol

: 928621-28-7
(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 89 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 0 °C

2.1: 77 percent / CH₂Cl₂ / 72 h / -78 - 23 °C

3.1: 85 percent / toluene / 24 h / 115 °C

4.1: 70 percent / NIS / CHCl₃ / 23 °C

5.1: 88 percent / n-Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 4 h / -78 °C

6.1: 70 percent / DDQ; aq. buffer / CH₂Cl₂ / 0 - 23 °C / pH 7

7.1: 70 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 23 °C

8.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C

8.2: 77 percent / tetrahydrofuran / cooling

9.1: 88 percent / K₂CO₃ / 5 h / 23 °C

10.1: imidazole / CH₂Cl₂ / 18 h / 23 °C

With 1H-imidazole; 2,6-dimethylpyridine; N-iodo-succinimide; triethyl borane; tri-n-butyl-tin hydride; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; 8.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol0629869

Reference yield:

: 928621-19-6
2-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-4-(tert-butyl-diphenyl-silanyloxy)-1-vinyl-butyl]-4,4,5,5-tetraphenyl-[1,3,2]dioxaborolane

: 928621-28-7
(2E,4E,6E,8E)-(11S,12S,13R,15S,17R)-11,15,17-tris-(tert-butyl-dimethyl-silanyloxy)-19-(tert-butyl-diphenyl-silanyloxy)-13-hydroxy-12-methyl-nonadeca-2,4,6,8-tetraenoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 77 percent / CH₂Cl₂ / 72 h / -78 - 23 °C

2.1: 85 percent / toluene / 24 h / 115 °C

3.1: 70 percent / NIS / CHCl₃ / 23 °C

4.1: 88 percent / n-Bu₃SnH; Et₃B / tetrahydrofuran; hexane / 4 h / -78 °C

5.1: 70 percent / DDQ; aq. buffer / CH₂Cl₂ / 0 - 23 °C / pH 7

6.1: 70 percent / Dess-Martin periodinane / CH₂Cl₂ / 0 - 23 °C

7.1: LHMDS / tetrahydrofuran / 0.25 h / -78 °C

7.2: 77 percent / tetrahydrofuran / cooling

8.1: 88 percent / K₂CO₃ / 5 h / 23 °C

9.1: imidazole / CH₂Cl₂ / 18 h / 23 °C

With 1H-imidazole; N-iodo-succinimide; triethyl borane; tri-n-butyl-tin hydride; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; chloroform; toluene; 7.2: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/ol0629869