(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

Base Information

Chemical Name:(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido
CAS No.:537665-57-9
Molecular Formula:C₄₀H₆₂O₂Si
Molecular Weight:603.017
Hs Code.:

Synonyms:(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

Chemical Property:

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Technology Process of (E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

There total 1 articles about (E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido 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: 98.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 485322-69-8
(E,E,3R,3R)-2,3-oxido-7,11-tetracosadien-1-ol

: 537665-57-9
(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

Guidance literature:: With 1H-imidazole; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;
DOI:10.1016/S0040-4020(03)00135-2

Reference yield:

: 537665-57-9
(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

: 537665-49-9
muconin 4-O-(t-butyldiphenylsilyl)-22-O-(methoxymethyl) diether

Guidance literature:: Multi-step reaction with 17 steps

1.1: AD-mix β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 14 h / 0 °C

2.1: d-camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

3.1: d-camphorsulfonic acid / methanol / 18 h / 20 °C

4.1: 171 mg / d-camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 6 h / 20 °C

6.1: 23.6 mg / Zn(BH₄)2 / diethyl ether / 0.5 h / -10 °C

7.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

8.1: AcOH / H₂O / 24 h / 20 °C

9.1: NaOMe / methanol / 20 - 50 °C

10.1: 88 mg / d-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 20 °C

11.1: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

12.1: 98 percent / AcOH / H₂O / 12 h / 20 °C

13.1: benzoyl chloride; pyridine / CH₂Cl₂ / 12 h / -20 - 5 °C

13.2: methanesulfonyl chloride; pyridine / CH₂Cl₂ / 7 h / -20 - 0 °C

13.3: 83 percent / NaOH / H₂O; tetrahydrofuran; methanol / 17 h / -20 - 5 °C

14.1: tetrahydrofuran; hexane / 1 h / -78 °C

14.2: 232 mg / BF₃*Et₂O / tetrahydrofuran / 2 h / -78 °C

15.1: 199 mg / K₂CO₃ / methanol / 5 h / 20 °C

16.1: 79 percent / Et₃N; CuI / (Ph₃P)2PdCl₂ / 2 h / 20 °C

17.1: 85 percent / H₂; (Ph₃P)3RhCl / benzene; ethanol / 7 h / 20 °C

With pyridine; dmap; copper(l) iodide; Wilkinson's catalyst; zinc(II) tetrahydroborate; methanesulfonamide; (1S)-10-camphorsulfonic acid; hydrogen; sodium methylate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; benzoyl chloride; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4020(03)00135-2

Reference yield:

: 537665-57-9
(E,E,3R,3R)-1-t-butyldiphenylsilyloxy-7,11-tetracosadien-2,3-oxido

: 485322-68-7
(S)-3-((E)-(2R,10S)-2-(tert-Butyl-diphenyl-silanyloxy)-10-hydroxy-10-{(2S,6R)-6-[(2R,5R)-5-((R)-1-methoxymethoxy-tridecyl)-tetrahydro-furan-2-yl]-tetrahydro-pyran-2-yl}-dec-5-en-7-ynyl)-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 16 steps

1.1: AD-mix β; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 14 h / 0 °C

2.1: d-camphorsulfonic acid / CH₂Cl₂ / 2 h / 20 °C

3.1: d-camphorsulfonic acid / methanol / 18 h / 20 °C

4.1: 171 mg / d-camphorsulfonic acid / CH₂Cl₂ / 5 h / 20 °C

5.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 6 h / 20 °C

6.1: 23.6 mg / Zn(BH₄)2 / diethyl ether / 0.5 h / -10 °C

7.1: 97 percent / N,N-dimethylaminopyridine; Et₃N / CH₂Cl₂ / 12 h / 0 - 20 °C

8.1: AcOH / H₂O / 24 h / 20 °C

9.1: NaOMe / methanol / 20 - 50 °C

10.1: 88 mg / d-camphorsulfonic acid / CH₂Cl₂ / 0.5 h / 20 °C

11.1: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 12 h / 20 °C

12.1: 98 percent / AcOH / H₂O / 12 h / 20 °C

13.1: benzoyl chloride; pyridine / CH₂Cl₂ / 12 h / -20 - 5 °C

13.2: methanesulfonyl chloride; pyridine / CH₂Cl₂ / 7 h / -20 - 0 °C

13.3: 83 percent / NaOH / H₂O; tetrahydrofuran; methanol / 17 h / -20 - 5 °C

14.1: tetrahydrofuran; hexane / 1 h / -78 °C

14.2: 232 mg / BF₃*Et₂O / tetrahydrofuran / 2 h / -78 °C

15.1: 199 mg / K₂CO₃ / methanol / 5 h / 20 °C

16.1: 79 percent / Et₃N; CuI / (Ph₃P)2PdCl₂ / 2 h / 20 °C

With pyridine; dmap; copper(l) iodide; zinc(II) tetrahydroborate; methanesulfonamide; (1S)-10-camphorsulfonic acid; sodium methylate; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; benzoyl chloride; acetic acid; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; N-ethyl-N,N-diisopropylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol;
DOI:10.1016/S0040-4020(03)00135-2