(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

Base Information

• Chemical Name: (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
• CAS No.: 1315614-15-3
• Molecular Formula: C₂₅H₂₅N₃O₁₂S₂
• Molecular Weight: 623.618

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 28 articles about (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 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:

C24H23N3O10S + methanesulfonyl chloride (124-63-0) → (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 (1315614-15-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1139/v11-071

Reference yield:

isovanillin (621-59-0) → (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 (1315614-15-3)

Guidance literature:

Multi-step reaction with 11 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

10.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C / Inert atmosphere

11.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °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; water; 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:

2-bromo-3-(1,3-dioxolan-2-ylmethyl)-6-methoxyphenol (1315613-93-4) → (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 (1315614-15-3)

Guidance literature:

Multi-step reaction with 7 steps

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

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

2.2: 16 h / 0 - 25 °C / Inert atmosphere

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

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

5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 4 h / 80 °C / Inert atmosphere

6.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tributylphosphine; tri-tert-butyl phosphine; di-isopropyl azodicarboxylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 1.1: Mitsunobu reaction / 2.1: Heck coupling reaction;

DOI:10.1139/v11-071

upstream raw materials:

isovanillin

2-(2,2-dimethyl-3a,6,7,7a-tetrahydrobenzo[d][1,3]dioxol-4-yl)-N-methylethanamine

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

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