(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

Base Information

Chemical Name:(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol
CAS No.:179945-16-5
Molecular Formula:C₂₀H₃₄O₃Si
Molecular Weight:350.574
Hs Code.:

Synonyms:(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

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Chemical Property of (E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

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Technology Process of (E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

There total 7 articles about (E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol 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: 97.0%

: 179945-15-4
(4R,5S,E)-ethyl 6-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4-methylhex-2-enoate

: 179945-16-5
(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/jo9606113

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 179945-16-5
(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) dibutylboron triflate, triethylamine / 1.) CH₂Cl₂, 0 deg C, 2.) CH₂Cl₂, -78 -> 0 deg C

2: 99 percent / trimethylaluminum / tetrahydrofuran; toluene; CH₂Cl₂ / 1.5 h / 0 °C

3: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

4: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

5: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

6: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

With 1H-imidazole; di-n-butylboryl trifluoromethanesulfonate; potassium tert-butylate; trimethylaluminum; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9606113

Reference yield:

: 157318-10-0
(4S,5R)-3-((2S,3S)-4-Benzyloxy-3-hydroxy-2-methyl-butyryl)-4-methyl-5-phenyl-oxazolidin-2-one

: 179945-16-5
(E)-(4R,5S)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / trimethylaluminum / tetrahydrofuran; toluene; CH₂Cl₂ / 1.5 h / 0 °C

2: 100 percent / imidazole / dimethylformamide / 5.5 h / 23 °C

3: 99 percent / diisobutylaluminum hydride / tetrahydrofuran; hexane / 2 h / -78 °C

4: 1.) potassium tert-butoxide / 1.) THF, room temperature, 1 h, 2.) THF, -78 -> 0 deg C

5: 97 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

With 1H-imidazole; potassium tert-butylate; trimethylaluminum; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo9606113