3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate

Base Information

• Chemical Name: 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate
• CAS No.: 1310878-75-1
• Molecular Formula: C₃₅H₄₂N₄O₁₆S₂
• Molecular Weight: 838.868
• Mol file: 1310878-75-1.mol

Synonyms:3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate

Chemical Property of 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate

There total 15 articles about 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate 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: 76.0%

1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-3-(2-hydroxyethyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate (1310878-68-2) + N-((2S)-4-ethyl-2,3-dihydrofuran-2-ylmethyl)-2,4-dinitrobenzenesulfonamide (221903-32-8) → 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate (1310878-75-1)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; benzene; at 0 - 20 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201100981

Reference yield:

5-((E)-2-(ethoxycarbonyl)vinyl)-4-isocyano-2,3-dimethoxyphenyl methanesulfonate (1310878-72-8) → 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate (1310878-75-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / acetonitrile / 0.5 h / Inert atmosphere; Reflux

1.2: 20 °C / Inert atmosphere

2.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 0 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / dichloromethane / 1.33 h / 20 °C / Inert atmosphere

4.1: dmap / acetonitrile / 0 - 20 °C / Inert atmosphere

5.1: copper(l) iodide; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); trifuran-2-yl-phosphane / N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide / 10 h / 20 - 80 °C / Inert atmosphere

6.1: camphor-10-sulfonic acid / methanol / 1 h / 20 °C / Inert atmosphere

7.1: triphenylphosphine; diethylazodicarboxylate / toluene; benzene / 1 h / 0 - 20 °C / Inert atmosphere

With dmap; copper(l) iodide; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); trifuran-2-yl-phosphane; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 5.1: Stille coupling / 7.1: Mitsunobu reaction;

DOI:10.1002/anie.201100981

Reference yield:

methyl 3,5-dihydroxy-4-methoxy-2-nitro-benzoate (1100771-88-7) → 3-(2-(((S)-4-ethyl-2,3-dihydrofuran-2-yl)methyl(2,4-dinitrobenzenesulfonyl)amino)ethyl)-1-(tert-butoxycarbonyl)-2-(1-(methoxycarbonyl)vinyl)-6,7-dimethoxy-1H-indol-5-yl methanesulfonate (1310878-75-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 2,6-dimethylpyridine / tetrahydrofuran; N,N-dimethyl-formamide / 2 h / 20 °C / Cooling with ice; Inert atmosphere

2.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 1.5 h / 20 °C / Cooling with ice; Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.42 h / 20 °C / Inert atmosphere

4.1: triethylamine / dichloromethane / 20 °C / Cooling with ice; Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane; toluene / 0.92 h / -78 °C / Inert atmosphere

6.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Molecular sieve

7.1: toluene / 0.33 h / 20 °C / Inert atmosphere

8.1: acetic acid; zinc / dichloromethane / 0.42 h / 0 - 20 °C / Inert atmosphere

9.1: acetic anhydride / 2 h / 50 °C / Inert atmosphere

9.2: 0.25 h / 0 °C / Inert atmosphere

9.3: 1 h / Cooling with ice; Inert atmosphere

10.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / acetonitrile / 0.5 h / Inert atmosphere; Reflux

10.2: 20 °C / Inert atmosphere

11.1: diisobutylaluminium hydride / dichloromethane; toluene / -78 - 0 °C / Inert atmosphere

12.1: camphor-10-sulfonic acid / dichloromethane / 1.33 h / 20 °C / Inert atmosphere

13.1: dmap / acetonitrile / 0 - 20 °C / Inert atmosphere

14.1: copper(l) iodide; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); trifuran-2-yl-phosphane / N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide / 10 h / 20 - 80 °C / Inert atmosphere

15.1: camphor-10-sulfonic acid / methanol / 1 h / 20 °C / Inert atmosphere

16.1: triphenylphosphine; diethylazodicarboxylate / toluene; benzene / 1 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; dmap; copper(l) iodide; tetrapropylammonium perruthennate; trans-benzyl(chloro)-bis(triphenylphosphine)palladium(II); trifuran-2-yl-phosphane; 2,2'-azobis(isobutyronitrile); camphor-10-sulfonic acid; potassium tert-butylate; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; acetic anhydride; diisobutylaluminium hydride; acetic acid; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; benzene; 7.1: Wittig reaction / 14.1: Stille coupling / 16.1: Mitsunobu reaction;

DOI:10.1002/anie.201100981

upstream raw materials:

methyl 3,5-dihydroxy-4-methoxy-2-nitro-benzoate

5-((E)-2-(ethoxycarbonyl)vinyl)-2,3-dimethoxy-4-nitrophenyl methanesulfonate

5-((E)-2-(ethoxycarbonyl)vinyl)-4-isocyano-2,3-dimethoxyphenyl methanesulfonate

3-((ethoxycarbonyl)methyl)-2-iodo-6,7-dimethoxy-1H-indol-5-yl methanesulfonate