(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

Base Information

Chemical Name:(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
CAS No.:442159-47-9
Molecular Formula:C₄₁H₇₄O₇Si₃
Molecular Weight:763.291
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

Chemical Property:

Purity/Quality:

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Technology Process of (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

There total 13 articles about (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 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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 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

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; 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

: 442159-47-9
(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

Guidance literature:: Multi-step reaction with 9 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

With 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; 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

Reference yield:

: 442159-37-7
(R)-4-benzyl-3-((2R,3R,E)-3-hydroxy-2,4-dimethylhex-4-enoyl)oxazolidin-2-one

: 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

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; manganese(IV) oxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; 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