N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

Base Information

• Chemical Name: N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide
• CAS No.: 1315614-14-2
• Molecular Formula: C₂₆H₂₇N₃O₁₁S
• Molecular Weight: 589.58

Synonyms:

Chemical Property of N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

There total 15 articles about N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide 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:

N-(2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide (1315614-13-1) → N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide (1315614-14-2)

Guidance literature:

With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In ethyl acetate; at 80 ℃; for 4h; Inert atmosphere;

DOI:10.1139/v11-071

Reference yield:

isovanillin (621-59-0) → N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide (1315614-14-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-Bromosuccinimide / chloroform / Inert atmosphere; Reflux

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C / Inert atmosphere

3.1: tert.-butyl lithium / tetrahydrofuran / 0.42 h / -78 °C / Inert atmosphere

3.2: 3.58 h / 0 °C / Inert atmosphere; Reflux

4.1: toluene-4-sulfonic acid / tetrahydrofuran / 2 h / Inert atmosphere; Reflux

5.1: tributylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 4 - 25 °C / Inert atmosphere

6.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; potassium carbonate / toluene / 16 h / 110 °C / Inert atmosphere

6.2: 16 h / 0 - 25 °C / Inert atmosphere

7.1: trifluoroacetic acid / dichloromethane / 0.42 h / 0 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / Inert atmosphere

9.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 80 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; N-Bromosuccinimide; tributylphosphine; tri-tert-butyl phosphine; di-isopropyl azodicarboxylate; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; chloroform; ethyl acetate; toluene; 3.1: Wittig reaction / 3.2: Wittig reaction / 5.1: Mitsunobu reaction / 6.1: Heck coupling reaction;

DOI:10.1139/v11-071

Reference yield:

(4S,4aS,9bR)-9-((1,3-dioxolan-2-yl)methyl)-6-methoxy-9b-(2-(methylamino)ethyl)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-4-ol (1315614-04-0) → N-(2-((5aS,9aR)-1-((1,3-dioxolan-2-yl)methyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide (1315614-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.33 h / Inert atmosphere

2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 80 °C / Inert atmosphere

With N-ethyl-N,N-diisopropylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; ethyl acetate;

DOI:10.1139/v11-071

upstream raw materials:

isovanillin

tert-butyl 2-((5'S,6'S)-6'-(3''-((1,3-dioxolan-2-yl)methyl)-2''-bromo-6''-methoxyphenoxy)-5'-(tert-butyldimethylsilyloxy)cyclohex-1'-enyl)ethyl(methyl)carbamate

tert-butyl 2-((5aS,6S,9aR)-1-((1,3-dioxolan-2-yl)methyl)-6-hydroxy-4-methoxy-5a,6,7,9a tetrahydrodibenzo[b,d]furan-9a-yl)ethyl(methyl)carbamate

(4S,4aS,9bR)-9-((1,3-dioxolan-2-yl)methyl)-6-methoxy-9b-(2-(methylamino)ethyl)-3,4,4a,9b-tetrahydrodibenzo[b,d]furan-4-ol

Downstream raw materials:

(2a⁽²⁾R,6aS,9aS)-5-Methoxy-2a2-(2-(N-methyl-2,4-dinitrophenylsulfonamido)ethyl)-7-oxo-1,2,2a⁽²⁾,6a,7,9a-hexahydrophenanthro[4,5-bcd]furan-1-yl methanesulfonate

N-(2-((2a⁽¹⁾R,5aS)-7-methoxy-5-oxo-1,2a1,5,5a-tetrahydrophenanthro[4,5-bcd]furan-2a1-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

N-(2-((2a1R,5aS)-7-methoxy-5-oxo-2a1,4,5,5a-tetrahydrophenanthro[4,5-bcd]furan-2a1-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

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