(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

Base Information

Chemical Name:(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol
CAS No.:294863-20-0
Molecular Formula:C₂₆H₃₇NO₃Si
Molecular Weight:439.67
Hs Code.:

Synonyms:(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

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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 (S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

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Technology Process of (S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

There total 7 articles about (S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-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: 84.5%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 294863-19-7
(S)-4-(5-benzyloxy-1-methylindol-3-yl)butane-1,2-diol

: 294863-20-0
(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/jm0306374

Reference yield:

: 58630-07-2
5-(benzyloxy)-1-methyl-1H-indole-3-carbaldehyde

: 294863-20-0
(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: 86.3 percent / NaH / dimethylformamide / 20 °C

2.1: 90 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 1.5 h / 20 °C / 1520 Torr

3.1: 77 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

4.1: n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

4.2: 87.7 percent / tetrahydrofuran / 2 h / 20 °C

5.1: 53.5 percent / AD-mix-α; water / 2-methyl-propan-2-ol / 4 h / 0 °C

6.1: 84.5 percent / imidazole / dimethylformamide / 0 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; water; hydrogen; sodium hydride; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Wittig-Horner reaction / 4.2: Wittig reaction / 5.1: Sharpless asymmetric hydroxylation;
DOI:10.1021/jm0306374

Reference yield:

: 742105-16-4
ethyl 3-(5-benzyloxy-1-methylindol-3-yl)acrylate

: 294863-20-0
(S)-4-(5-benzyloxy-1-methylindol-3-yl)-1-(tert-butyldimethylsilyloxy)butan-2-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 90 percent / H₂ / Pd/C / ethanol; tetrahydrofuran / 1.5 h / 20 °C / 1520 Torr

2.1: 77 percent / DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

3.1: n-BuLi / tetrahydrofuran / 2 h / -78 - 20 °C

3.2: 87.7 percent / tetrahydrofuran / 2 h / 20 °C

4.1: 53.5 percent / AD-mix-α; water / 2-methyl-propan-2-ol / 4 h / 0 °C

5.1: 84.5 percent / imidazole / dimethylformamide / 0 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; water; hydrogen; diisobutylaluminium hydride; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.2: Wittig reaction / 4.1: Sharpless asymmetric hydroxylation;
DOI:10.1021/jm0306374