(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

Base Information

Chemical Name:(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol
CAS No.:192052-17-8
Molecular Formula:C₂₂H₃₈O₃Si
Molecular Weight:378.627
Hs Code.:

Synonyms:(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

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Chemical Property of (E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

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Technology Process of (E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

There total 3 articles about (E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol 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:

: 70925-46-1,56161-69-4
(2E)-2-methyl-5-phenyl-2-pentenal

: 192052-17-8
(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium tert-butoxide; n-butyllithium; (-)-diisopinylcampheylmethoxyborane / tetrahydrofuran; hexane / -78 °C

1.2: boron trifluoride etherate / tetrahydrofuran; hexane; diethyl ether / 15 h / -78 °C

1.3: H₂O₂; aq. NaOH / tetrahydrofuran; hexane; diethyl ether / 3 h / 20 °C

2.1: imidazole / dimethylformamide / 20 °C

3.1: AD-mix-β / H2O; 2-methyl-propan-2-ol / 24 h / 20 °C

With 1H-imidazole; n-butyllithium; AD-mix-β; potassium tert-butylate; (-)-B-methoxydiisopinocampheylborane; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Addition / 1.2: Addition / 1.3: Oxidation / 2.1: Etherification / 3.1: Oxidation;
DOI:10.1021/jo000453m

Reference yield:

: 297153-44-7
(3R,4R,5E)-4-hydroxy-8-phenyl-3,5-dimethyl-1,5-octadiene

: 192052-17-8
(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 20 °C

2: AD-mix-β / H2O; 2-methyl-propan-2-ol / 24 h / 20 °C

With 1H-imidazole; AD-mix-β; In water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Etherification / 2: Oxidation;
DOI:10.1021/jo000453m

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 192052-17-8
(E)-(3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3,5-dimethyl-8-phenyl-oct-5-ene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 83 percent / imidazole

2: 86 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O

With 1H-imidazole; AD-mix-β; In water; tert-butyl alcohol;
DOI:10.1021/ja972603p