(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

Base Information

Chemical Name:(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane
CAS No.:354538-32-2
Molecular Formula:C₂₃H₂₉BrN₄O₃SSi
Molecular Weight:549.564
Hs Code.:

Synonyms:(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

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Chemical Property of (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

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Technology Process of (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

There total 6 articles about (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane 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: 87.0%

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

: 354538-32-2
(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

Guidance literature:: With diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene; at -20 - 20 ℃;
DOI:10.1021/jo010265b

Reference yield:

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

: 354538-32-2
(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

Guidance literature:: Multi-step reaction with 5 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

5.1: 87 percent / Ph₃P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C

With 1H-imidazole; AD-mix-α; n-butyllithium; diphenylphosphoranyl azide; potassium carbonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 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

: 354538-32-2
(1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane

Guidance literature:: Multi-step reaction with 5 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

5.1: 87 percent / Ph₃P; diethyl azodicarboxylate; diphenylphosphoryl azide / tetrahydrofuran; toluene / -20 - 20 °C

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