354538-27-5

Basic information

• Product Name: 6-bromo-1-tosyl-3-vinyl-1H-indole
• Synonyms: 6-bromo-1-tosyl-3-vinyl-1H-indole
• CAS NO: 354538-27-5
• Molecular Weight: 376.274
• Mol File: 354538-27-5.mol

Chemical Properties

• CAS DataBase Reference: 6-bromo-1-tosyl-3-vinyl-1H-indole(CAS DataBase Reference)
• NIST Chemistry Reference: 6-bromo-1-tosyl-3-vinyl-1H-indole(354538-27-5)
• EPA Substance Registry System: 6-bromo-1-tosyl-3-vinyl-1H-indole(354538-27-5)

Safety Data

• Hazardous Substances Data: 354538-27-5(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 17826-04-9 6-bromo-1H-indole-3-carbaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 158991-81-2 6-bromo-N-(1-p-toluenesulphonyl)-indole-3-carboxaldehyde 

Downstream Products

• 354538-23-1 (R)-6-bromo-N-[(N-tosyl-6-bromoindol-3-yl)azidoethyl]-α-oxoindole-3-acetamide 
• 354538-37-7 (R)-3-(6-bromoindol-3-yl)-6-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 
• 354538-35-5 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(4-methylphenylsulfonyl)oxy]ethylamine 
• 354538-36-6 (1R)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-2-azidoethylamine 
• 354538-32-2 (1R)-1-(N-tosyl-6-bromoindol-3-yl)-1-azido-2-[(tert-butyldimethylsilyl)oxy]ethane 
• 354538-30-0 (1S)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tert-butyldimethylsilyl)oxy]-1-ethanol 
• 354538-34-4 (R)-2-azido-2-(N-tosyl-6-bromoindol-3-yl)-1-ethanol 
• 1026187-62-1 2-azido-1-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-ethylamine 
• 404888-95-5 (S)-N-[2-azido-2-(N-tosyl-6-bromo-indol-3-yl)ethyl]-2-(6-bromo-1H-indol-3-yl)-2-oxoacetamide 
• 404888-96-6 (S)-3-(6-bromoindol-3-yl)-5-(N-tosyl-6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone 
• 404888-85-3 (R)-1-(N-tosyl-6-bromoindol-3-yl)-2-[(tosyl)oxy]-1-ethanol 
• 404888-93-3 (S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine 
• 404888-90-0 1,1-dimethylethyl (1R)-N-[2-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate 
• 404888-89-7 (R)-1-(N-tosyl-6-bromoindol-3-yl)-2-azido-1-ethanol 

Relevant articles and documents

Asymmetric aminohydroxylation of vinyl indoles: A short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A

A useful approach for the direct enantioselective synthesis of (S)-N-Boc-protected α-indol-3-ylglycinols from vinyl indoles using the Sharpless asymmetric aminohydroxylation reaction, with enantioselectivities of up to 94% and isolated yields of up to 65%

Enantioselective synthesis for the (-)-antipode of the pyrazinone marine alkaloid, hamacanthin A

A short enantioselective total synthesis for the (-)-antipode of the antifungal marine alkaloid, hamacanthin A, (6R)-3,6-bis(6-bromoindol-3-yl)-5,6-dihydro-2(1H)-pyrazinone, is described. This synthesis proceeds through the coupling of 3-indolyl-αoxoacetyl chloride and 3-indolyl azidoethylamine, followed by intramolecular aza-Wittig type cyclization. A concise and useful approach for the synthesis of (1R)-1-(indol-3-yl)-2-azidoethylamine using the Sharpless asymmetric dihydroxylation reaction followed by stereospecific azidation is also presented.