(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

Base Information

Chemical Name:(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene
CAS No.:474958-73-1
Molecular Formula:C₂₀H₃₄O₄Si
Molecular Weight:366.573
Hs Code.:

Synonyms:(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

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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 (1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

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Technology Process of (1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

There total 7 articles about (1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene 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: 86.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 474958-72-0
(1R,2S)-2-(2-methoxy-ethoxymethoxy)-1-phenylbut-3-en-1-ol

: 474958-73-1
(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 4h;
DOI:10.1021/jo0259358

Reference yield:

: 77120-79-7
1-<(2-methoxyethoxy)methoxy>-2-propene

: 474958-73-1
(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

Guidance literature:: Multi-step reaction with 6 steps

1.1: sec-BuLi / tetrahydrofuran / 1 h / -78 °C

1.2: BF₃*Et₂O / tetrahydrofuran / -100 °C

2.1: tetrahydrofuran / 2 h / -100 °C

3.1: 42.8 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 10 h / 25 °C

4.1: 76 percent / PPh₃; DEAD / toluene / 3 h / -50 °C

5.1: 77.5 percent / NaOH / methanol; H₂O / 1 h / 20 °C

6.1: 86 percent / imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium hydroxide; dihydrogen peroxide; sec.-butyllithium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0259358

Reference yield:

: 100-52-7
benzaldehyde

: 474958-73-1
(1R,2S)-1-(tert-butyldimethylsilyloxy)-2-(methoxyethoxymethoxy)-1-phenyl-but-3-ene

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 2 h / -100 °C

2: 42.8 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 10 h / 25 °C

3: 76 percent / PPh₃; DEAD / toluene / 3 h / -50 °C

4: 77.5 percent / NaOH / methanol; H₂O / 1 h / 20 °C

5: 86 percent / imidazole / dimethylformamide / 4 h / 20 °C

With 1H-imidazole; sodium hydroxide; dihydrogen peroxide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0259358