(4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

Base Information

• Chemical Name: (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene
• CAS No.: 211758-69-9
• Molecular Formula: C₃₀H₃₄N₂O₄S
• Molecular Weight: 518.677

Synonyms:(4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

Chemical Property of (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

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Technology Process of (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene

There total 27 articles about (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.0^8,13]tetracosa-1⁽²⁴⁾,4,8,10,12,16,20,22-octaene 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:

2-methyl-4-nitropyridine N-oxide (5470-66-6) → (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(24),4,8,10,12,16,20,22-octaene (211758-69-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 84 percent / PCl₃ / CHCl₃ / 40 h / Ambient temperature

2: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

3: 83 percent / methanol / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

5: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

6: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

7: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

8: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

9: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

10: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

11: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

12: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

13: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

14: 98 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 50 h / Ambient temperature

15: 78 percent / tetra-n-butylammonium peroxymonosulfate / CH₂Cl₂ / 24 h / Ambient temperature

16: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 30 min, 2.) THF, reflux, 7 h

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetra-n-butylammonium peroxomonosulfate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; phosphorus trichloride; In tetrahydrofuran; methanol; dichloromethane; chloroform; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

2-methyl-4-nitro-pyridine (13508-96-8) → (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(24),4,8,10,12,16,20,22-octaene (211758-69-9)

Guidance literature:

Multi-step reaction with 15 steps

1: 50 percent / NaOH / dimethylsulfoxide / 0.5 h / 15 - 20 °C

2: 83 percent / methanol / Ambient temperature

3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

4: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

5: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

6: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

7: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

8: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

9: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

10: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

11: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

12: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

13: 98 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 50 h / Ambient temperature

14: 78 percent / tetra-n-butylammonium peroxymonosulfate / CH₂Cl₂ / 24 h / Ambient temperature

15: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 30 min, 2.) THF, reflux, 7 h

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium hydroxide; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetra-n-butylammonium peroxomonosulfate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jo9801770

Reference yield:

3-Benzenesulfonylmethyl-2-methyl-4-nitro-pyridine (88912-66-7) → (4E,16E)-7-Benzenesulfonyl-12,24-dimethoxy-9,21-diaza-tricyclo[18.4.0.08,13]tetracosa-1(24),4,8,10,12,16,20,22-octaene (211758-69-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 83 percent / methanol / Ambient temperature

2: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 1 h, then -78 to 0 deg C, 45 min, 2.) THF, hexane, 1.25 h

3: 94 percent / Na/Hg, Na₂HPO₄ / methanol / 2.5 h / Ambient temperature

4: 89 percent / OsO₄, NaIO₄ / tetrahydrofuran / 7 h / 0 - 20 °C

5: 81 percent / tetrahydrofuran / 4.5 h / -50 - 20 °C

6: 95 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 6.5 h / Ambient temperature

7: 97 percent / m-CPBA / CH₂Cl₂ / 3 h / Ambient temperature

8: 1.) p-TsCl, Et₃N / 1.) CH₂Cl₂, -50 deg C, 5 h, 2.) DMF, room temp., 12 h

9: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 70 min, 2.) THF, reflux, 4 h

10: 66 percent / Na/Hg, Na₂HPO₄ / methanol / 2 h / Ambient temperature

11: 100 percent / n-Bu₄NF / tetrahydrofuran / 5.5 h / 0 °C

12: 98 percent / Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 50 h / Ambient temperature

13: 78 percent / tetra-n-butylammonium peroxymonosulfate / CH₂Cl₂ / 24 h / Ambient temperature

14: 1.) NaHMDS, 2.) Pd₂(dba)3*CHCl₃, 1,2-bis(diphenylphosphino)ethane / 1.) THF, -78 deg C, 30 min, 2.) THF, reflux, 7 h

With dmap; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; sodium periodate; disodium hydrogenphosphate; sodium amalgam; osmium(VIII) oxide; n-butyllithium; tetra-n-butylammonium peroxomonosulfate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; triethylamine; p-toluenesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; 1,2-bis-(diphenylphosphino)ethane; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo9801770

upstream raw materials:

2,2-Dimethyl-propionic acid 1-(2-{2-[(E)-6-(2-benzenesulfonylmethyl-4-methoxy-pyridin-3-yl)-hex-3-enyl]-4-methoxy-pyridin-3-yl}-ethyl)-allyl ester

2,2-Dimethyl-propionic acid (E)-5-{2-[(E)-6-(2-benzenesulfonylmethyl-4-methoxy-pyridin-3-yl)-hex-3-enyl]-4-methoxy-pyridin-3-yl}-pent-2-enyl ester

2-methyl-4-nitro-pyridine

2-methyl-4-nitropyridine N-oxide

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