(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

Base Information

Chemical Name:(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine
CAS No.:404888-93-3
Molecular Formula:C₂₂H₂₄BrN₅O₄S
Molecular Weight:534.434
Hs Code.:

Synonyms:(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

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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)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

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Technology Process of (S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

There total 7 articles about (S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine 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: 83.0%

: 404888-90-0
1,1-dimethylethyl (1R)-N-[2-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate

: 404888-93-3
(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

Guidance literature:: With diphenylphosphoranyl azide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at -20 - 20 ℃;
DOI:10.1021/jo0108109

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 404888-93-3
(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

Guidance literature:: Multi-step reaction with 2 steps

1: 600 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

2: 83 percent / diphenylphosphoryl azide; DEAD; PPh₃ / tetrahydrofuran / -20 - 20 °C

With diphenylphosphoranyl azide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; 2: Mitsunobu reaction;
DOI:10.1021/jo0108109

Reference yield:

: 354538-27-5
6-bromo-1-tosyl-3-vinyl-1H-indole

: 404888-93-3
(S)-N-(tert-butyloxycarbonyl)-1-(N-tosyl-6-bromoindol-3-yl)-1-azidoethylamine

Guidance literature:: Multi-step reaction with 6 steps

1: 89 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O

2: 75 percent / CH₂Cl₂ / 6 h / Heating

3: 80 percent / NaN₃ / dimethylformamide / 12 h / 80 °C

4: SnCl₂*2H₂O / methanol / 20 h / 30 °C

5: 600 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

6: 83 percent / diphenylphosphoryl azide; DEAD; PPh₃ / tetrahydrofuran / -20 - 20 °C

With sodium azide; AD-mix-β; diphenylphosphoranyl azide; triethylamine; triphenylphosphine; tin(ll) chloride; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 1: Sharpless dihydroxylation / 6: Mitsunobu reaction;
DOI:10.1021/jo0108109