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

Base Information

Chemical Name:(8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-tetradeca-8,12-dienoic acid benzyl ester
CAS No.:442159-50-4
Molecular Formula:C₃₈H₆₆O₆Si₂
Molecular Weight:675.109
Hs Code.:

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

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

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

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

There total 16 articles about (8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-tetradeca-8,12-dienoic 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:

: (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-8,12-dienoic acid benzyl ester

: 442159-50-4
(8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-tetradeca-8,12-dienoic acid benzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; ethyl acetate; at 20 ℃; for 24h;
DOI:10.1055/s-2002-22724

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 442159-50-4
(8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-tetradeca-8,12-dienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / -78 - 20 °C

2: 88 percent / LiAlH₄ / diethyl ether / 1 h / -78 - 0 °C

3: 93 percent / NaIO₄ / methanol; aq. phosphate buffer / 6 h / 20 °C

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

5: 75 percent / Et₃NSO₂NCO₂Me / benzene / 2 h / 20 °C

6: H₂ / [(Ph₃P)CuH]6 / H₂O; benzene / 12 h / 20 °C

7: TBAF / tetrahydrofuran; ethyl acetate / 24 h / 20 °C

With 2,6-dimethylpyridine; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; Burgess Reagent; tetrabutyl ammonium fluoride; hydrogen; diisopropylamine; zinc(II) chloride; (triphenylphosphine)copper(I) hydride hexamer; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1055/s-2002-22724

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 442159-50-4
(8E,12E)-(2S,6S,7S,10S,11R)-7,11-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-2,6,8,10,12-pentamethyl-3-oxo-tetradeca-8,12-dienoic acid benzyl ester

Guidance literature:: Multi-step reaction with 14 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

13: H₂ / [(Ph₃P)CuH]6 / H₂O; benzene / 12 h / 20 °C

14: TBAF / tetrahydrofuran; ethyl acetate / 24 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; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; diisopropylamine; zinc(II) chloride; palladium on activated charcoal; (triphenylphosphine)copper(I) hydride hexamer; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; benzene;
DOI:10.1055/s-2002-22724