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

N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-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,6S,9aR)-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide
  • CAS No.:1315614-18-6
  • Molecular Formula:C26H31N3O11S
  • Molecular Weight:593.612
  • Hs Code.:
N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide

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

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

There total 14 articles about N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-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: 86.0%

methanol
67-56-1

methanol

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,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

N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide
1315614-18-6

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

Guidance literature:
With toluene-4-sulfonic acid; for 72h; Inert atmosphere; Reflux;
DOI:10.1139/v11-071

Reference yield:

isovanillin
621-59-0

isovanillin

N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide
1315614-18-6

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

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: toluene-4-sulfonic acid / 72 h / Inert atmosphere; Reflux
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; In tetrahydrofuran; dichloromethane; chloroform; 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:

C<sub>11</sub>H<sub>17</sub>BrO<sub>2</sub>
1315613-94-5

C11H17BrO2

N-(2-((5aS,6S,9aR)-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-5a,6,7,9a-tetrahydrodibenzo[b,d]furan-9a-yl)ethyl)-N-methyl-2,4-dinitrobenzenesulfonamide
1315614-18-6

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

Guidance literature:
Multi-step reaction with 9 steps
1.1: potassium carbonate / tetrahydrofuran / 18.25 h / -40 - 25 °C / Inert atmosphere
2.1: hydrogenchloride / ethanol; water / 4 h / Inert atmosphere
3.1: ethanol; water / 4 h / Inert atmosphere
4.1: 1H-imidazole / dichloromethane / -78 - 25 °C / Inert atmosphere
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: toluene-4-sulfonic acid / 72 h / Inert atmosphere; Reflux
With 1H-imidazole; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium(0); tributylphosphine; tri-tert-butyl phosphine; di-isopropyl azodicarboxylate; potassium carbonate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 5.1: Mitsunobu reaction / 6.1: Heck coupling reaction;
DOI:10.1139/v11-071
upstream raw materials:

isovanillin

methanol

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

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

Downstream raw materials:

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

(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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