(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

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Chemical Name:(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester
CAS No.:1322744-58-0
Molecular Formula:C₂₇H₂₅N₃O₈S
Molecular Weight:551.577
Hs Code.:

Synonyms:(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

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Chemical Property of (S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

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Technology Process of (S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

There total 4 articles about (S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester 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: 31.0%

: 1322744-50-2
3-bromo-4-nitro-1-(toluene-4-sulfonyl)-1H-indole

: 56877-38-4
methyl N-((benzyloxy)carbonyl)-3-iodo-L-alaninate

: 1322744-58-0
(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

Guidance literature:: methyl N-((benzyloxy)carbonyl)-3-iodo-L-alaninate; With chloro-trimethyl-silane; ethylene dibromide; zinc; In N,N-dimethyl-formamide; at 20 ℃; for 2.5h;

3-bromo-4-nitro-1-(toluene-4-sulfonyl)-1H-indole; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; In N,N-dimethyl-formamide; at 35 ℃; for 4h;
DOI:10.1016/j.tet.2011.06.053

Reference yield:

: 81038-28-0
4-nitro-1-tosyl-1H-indole

: 1322744-58-0
(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: bromine / dichloromethane / 0.25 h / 0 °C

2.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl-formamide / 2.5 h / 20 °C

2.2: 4 h / 35 °C

With chloro-trimethyl-silane; bromine; ethylene dibromide; zinc; In dichloromethane; N,N-dimethyl-formamide; 2.2: Negishi cross-coupling;
DOI:10.1016/j.tet.2011.06.053

Reference yield:

: 98-59-9
p-toluenesulfonyl chloride

: 1322744-58-0
(S)-2-benzyloxycarbonylamino-3-[4-nitro-1-(toluene-4-sulfonyl)-1H-indol-3-yl]propionic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C

1.2: 2 h / 20 °C

2.1: bromine / dichloromethane / 0.25 h / 0 °C

3.1: chloro-trimethyl-silane; ethylene dibromide; zinc / N,N-dimethyl-formamide / 2.5 h / 20 °C

3.2: 4 h / 35 °C

With chloro-trimethyl-silane; bromine; sodium hydride; ethylene dibromide; zinc; In dichloromethane; N,N-dimethyl-formamide; 3.2: Negishi cross-coupling;
DOI:10.1016/j.tet.2011.06.053