(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

Base Information

Chemical Name:(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate
CAS No.:1365533-65-8
Molecular Formula:C₃₃H₄₆N₂O₆SSi
Molecular Weight:626.89
Hs Code.:

Synonyms:(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

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Chemical Property of (1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

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Technology Process of (1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

There total 7 articles about (1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate 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:

: 1365533-64-7
(S)-tert-butyl 2-bromo-3-(3-((tert-butyldimethylsilyl)oxy)-2-(p-toluenesulfonamido)propyl)-1H-indole-1-carboxylate

: 78-94-4,25038-87-3
methyl vinyl ketone

: 1365533-65-8
(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

: 1365533-69-2
(1R,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

Guidance literature:: With palladium diacetate; triethylamine; triphenylphosphine; In toluene; at 110 ℃; for 16h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

: 79659-73-7
N-<(4-Methylphenyl)sulfonyl>tryptophan Methyl Ester

: 1365533-65-8
(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

: 1365533-69-2
(1R,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridinium hydrobromide perbromide / tetrahydrofuran; chloroform / 1 h / 0 °C

2.1: dmap / dichloromethane / 2 h / 20 °C

3.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 16 h / 0 - 20 °C

3.2: 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

5.1: palladium diacetate; triethylamine; triphenylphosphine / toluene / 16 h / 110 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; pyridinium hydrobromide perbromide; palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 5.1: domino Heck-aza-Michael reaction;
DOI:10.1016/j.tetlet.2012.01.037

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1365533-65-8
(1S,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

: 1365533-69-2
(1R,3S)-tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-1-(2-oxopropyl)-2-tosyl-3,4-dihydro-1H-pyrido[3,4-b]indole-9(2H)-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: pyridinium hydrobromide perbromide / tetrahydrofuran; chloroform / 1 h / 0 °C

3.1: dmap / dichloromethane / 2 h / 20 °C

4.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / 16 h / 0 - 20 °C

4.2: 20 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

6.1: palladium diacetate; triethylamine; triphenylphosphine / toluene / 16 h / 110 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; pyridinium hydrobromide perbromide; palladium diacetate; triethylamine; triphenylphosphine; In tetrahydrofuran; ethanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 6.1: domino Heck-aza-Michael reaction;
DOI:10.1016/j.tetlet.2012.01.037