N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

Base Information

Chemical Name:N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide
CAS No.:1310737-18-8
Molecular Formula:C₂₉H₂₇BrN₂O₆S₂
Molecular Weight:643.579
Hs Code.:

Synonyms:N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

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Chemical Property of N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

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Technology Process of N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

There total 6 articles about N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide 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:

: 1310737-17-7
(S,Z)-N-[6-(4-bromo-1-tosyl-1H-indol-3-yl)-2-(hydroxymethyl)hex-5-en-3-yn-1-yl]-4-methylbenzenesulfonamide

: N-[(S)-4-[(2R,3S)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

: 1310737-18-8
N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: With Shi's ketone; potassium peroxymonosulfate; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium hydroxide; In Dimethoxymethane; acetonitrile; at 0 ℃; for 22h; optical yield given as %de; diastereoselective reaction; aq. acetate buffer; Inert atmosphere;
DOI:10.1021/jo2008324

Reference yield:

: 181271-32-9
4-bromo-1-(4-toluenesulfonyl)indole-3-carboxaldehyde

: N-[(S)-4-[(2R,3S)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

: 1310737-18-8
N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: triphenylphosphine / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride / toluene / 8.5 h / 20 °C / Inert atmosphere

3.1: copper(l) iodide; dichloro bis(acetonitrile) palladium(II); diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

4.1: potassium peroxymonosulfate; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium hydroxide / Dimethoxymethane; acetonitrile / 22 h / 0 °C / aq. acetate buffer; Inert atmosphere

With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Shi's ketone; potassium peroxymonosulfate; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; diisopropylamine; triphenylphosphine; potassium hydroxide; In tetrahydrofuran; Dimethoxymethane; dichloromethane; toluene; acetonitrile; 3.1: Sonogashira coupling / 4.1: Shi epoxidation;
DOI:10.1021/jo2008324

Reference yield:

: 52488-36-5
4-bromo-1H-indole

: N-[(S)-4-[(2R,3S)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

: 1310737-18-8
N-[(S)-4-[(2S,3R)-(4-bromo-1-tosyl-1H-indol-3-yl)oxiran-2-yl]-2-(hydroxymethyl)but-3-yn-1-yl]-4-methylbenzenesulfonamide

Guidance literature:: Multi-step reaction with 6 steps

1.1: trichlorophosphate

2.1: dmap; triethylamine / dichloromethane

3.1: triphenylphosphine / dichloromethane / 0.25 h / -20 °C / Inert atmosphere

3.2: -78 - 20 °C / Inert atmosphere

4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride / toluene / 8.5 h / 20 °C / Inert atmosphere

5.1: copper(l) iodide; dichloro bis(acetonitrile) palladium(II); diisopropylamine / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

6.1: potassium peroxymonosulfate; Shi's ketone; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; potassium hydroxide / Dimethoxymethane; acetonitrile / 22 h / 0 °C / aq. acetate buffer; Inert atmosphere

With dmap; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Shi's ketone; potassium peroxymonosulfate; tri-n-butyl-tin hydride; tetra(n-butyl)ammonium hydrogensulfate; edetate disodium; triethylamine; diisopropylamine; triphenylphosphine; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; Dimethoxymethane; dichloromethane; toluene; acetonitrile; 1.1: Vilsmeier-Haack reaction / 5.1: Sonogashira coupling / 6.1: Shi epoxidation;
DOI:10.1021/jo2008324