(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

Base Information

Chemical Name:(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol
CAS No.:354538-30-0
Molecular Formula:C₂₃H₃₀BrNO₄SSi
Molecular Weight:524.551
Hs Code.:

Synonyms:(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

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Chemical Property of (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

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Technology Process of (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

There total 5 articles about (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol 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: 94.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 354538-26-4
(S)-1-(N-tosyl-6-bromoindol-3-yl)-1,2-ethanediol

: 354538-30-0
(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 12.5h;
DOI:10.1021/jo010265b

Reference yield:

: 17826-04-9
6-bromo-1H-indole-3-carbaldehyde

: 354538-30-0
(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / K₂CO₃ / butan-2-one / 3 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C

3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 12.5 h / 0 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; butanone; tert-butyl alcohol; 2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo010265b

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 354538-30-0
(1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / K₂CO₃ / butan-2-one / 3 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

2.2: 90 percent / tetrahydrofuran / 0.33 h / 0 °C

3.1: 92 percent / AD-mix-α / H2O; 2-methyl-propan-2-ol / 13 h / 0 - 20 °C

4.1: 94 percent / imidazole / CH₂Cl₂ / 12.5 h / 0 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; butanone; tert-butyl alcohol; 2.2: Wittig olefination / 3.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/jo010265b