(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

Base Information

Chemical Name:(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester
CAS No.:442159-48-0
Molecular Formula:C₄₁H₇₂O₆Si₃
Molecular Weight:745.276
Hs Code.:

(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

Synonyms:(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

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Chemical Property of (4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

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Technology Process of (4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

There total 14 articles about (4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl 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: 75.0%

: 442159-47-9
(8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-8,12-dienoic acid benzyl ester

: 442159-48-0
(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

Guidance literature:: With Burgess Reagent; In benzene; at 20 ℃; for 2h;
DOI:10.1055/s-2002-22724

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 442159-48-0
(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1: 92 percent / imidazole / dimethylformamide / 17 h / 80 °C

2: 92 percent / n-BuLi / tetrahydrofuran / 2.5 h / 0 °C

3: Et₃SiH / Pd/C / acetone / 5.5 h / 20 °C

4: benzene / 12 h / Heating

5: 98 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

6: 96 percent / MnO₂ / CH₂Cl₂ / 5 h / 20 °C

7: Me₂NEt / diethyl ether / 15 h / -78 - -20 °C

8: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / -78 - 20 °C

9: 88 percent / LiAlH₄ / diethyl ether / 1 h / -78 - 0 °C

10: 93 percent / NaIO₄ / methanol; aq. phosphate buffer / 6 h / 20 °C

11: iPr₂NH; n-BuLi; ZnCl₂ / tetrahydrofuran / 1 h / -78 - -50 °C

12: 75 percent / Et₃NSO₂NCO₂Me / benzene / 2 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; N,N-dimethyl-ethanamine; diisobutylaluminium hydride; diisopropylamine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1055/s-2002-22724

Reference yield:

: 442159-39-9
3-(tert-butyl-dimethyl-silanyloxy)-2,4-dimethyl-hex-4-enethioic acid S-ethyl ester

: 442159-48-0
(4E,8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2,6,8,10,12-pentamethyl-3-oxo-2-trimethylsilanyloxy-tetradeca-4,8,12-trienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: Et₃SiH / Pd/C / acetone / 5.5 h / 20 °C

2: benzene / 12 h / Heating

3: 98 percent / DIBALH / CH₂Cl₂ / 3 h / -78 °C

4: 96 percent / MnO₂ / CH₂Cl₂ / 5 h / 20 °C

5: Me₂NEt / diethyl ether / 15 h / -78 - -20 °C

6: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / -78 - 20 °C

7: 88 percent / LiAlH₄ / diethyl ether / 1 h / -78 - 0 °C

8: 93 percent / NaIO₄ / methanol; aq. phosphate buffer / 6 h / 20 °C

9: iPr₂NH; n-BuLi; ZnCl₂ / tetrahydrofuran / 1 h / -78 - -50 °C

10: 75 percent / Et₃NSO₂NCO₂Me / benzene / 2 h / 20 °C

With 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; N,N-dimethyl-ethanamine; diisobutylaluminium hydride; diisopropylamine; zinc(II) chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; acetone; benzene;
DOI:10.1055/s-2002-22724