1,2-Propanediol, 2-[(1S,6S)-9-[(4-methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl] -

Base Information

• Chemical Name: 1,2-Propanediol, 2-[(1S,6S)-9-[(4-methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl] -
• CAS No.: 916152-75-5
• Molecular Formula: C18H25NO4S
• Molecular Weight: 351.467
• Mol file: 916152-75-5.mol

Synonyms:

Chemical Property of 1,2-Propanediol, 2-[(1S,6S)-9-[(4-methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl] -

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-Propanediol, 2-[(1S,6S)-9-[(4-methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl] -

There total 13 articles about 1,2-Propanediol, 2-[(1S,6S)-9-[(4-methylphenyl)sulfonyl]-9-azabicyclo[4.2.1]non-2-en-2-yl] - 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: 59.0%

(1S,6S)-2-(2-propen-2-yl)-9-p-toluenesulfonyl-9-azabicyclo[4.2.1]non-2-ene (916152-66-4) → 2-[(1S,6S)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-en-2-yl]-propane-1,2-diol (916152-75-5)

Guidance literature:

(1S,6S)-2-(2-propen-2-yl)-9-p-toluenesulfonyl-9-azabicyclo[4.2.1]non-2-ene; With osmium(VIII) oxide; triethylamine; In tetrahydrofuran; at 20 ℃; for 64h;

With water; sodium hydrogensulfite; In tetrahydrofuran; for 2.5h; Heating;

DOI:10.1016/j.tet.2006.05.088

Reference yield:

(2S,5S)-5-But-3-enyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde (916152-71-1) → 2-[(1S,6S)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-en-2-yl]-propane-1,2-diol (916152-75-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 96 percent / PPh₃ / CH₂Cl₂ / 1.5 h / 0 °C

2.1: 80 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: 82 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C

4.1: 78 percent / (2-iPrO-3-PhC₆H₃CH=)(1,3-di-Mes-imidazolidin-2-ylidene)RuCl₂ / CH₂Cl₂ / 29 h / 20 °C

5.1: OsO₄; Et₃N / tetrahydrofuran / 64 h / 20 °C

5.2: 59 percent / NaHSO₃; H₂O / tetrahydrofuran / 2.5 h / Heating

With osmium(VIII) oxide; n-butyllithium; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; (2-iPrO-3-PhC₆H₃CH=)(1,3-di-Mes-imidazolidin-2-ylidene)RuCl₂; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.tet.2006.05.088

Reference yield:

[(2S,5S)-5-But-3-enyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol (916152-70-0) → 2-[(1S,6S)-9-(Toluene-4-sulfonyl)-9-aza-bicyclo[4.2.1]non-2-en-2-yl]-propane-1,2-diol (916152-75-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 86 percent / Dess-Martin periodinane / CH₂Cl₂ / 1.5 h / 20 °C

2.1: 96 percent / PPh₃ / CH₂Cl₂ / 1.5 h / 0 °C

3.1: 80 percent / BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

4.1: 82 percent / NaHMDS / tetrahydrofuran / 2 h / -78 °C

5.1: 78 percent / (2-iPrO-3-PhC₆H₃CH=)(1,3-di-Mes-imidazolidin-2-ylidene)RuCl₂ / CH₂Cl₂ / 29 h / 20 °C

6.1: OsO₄; Et₃N / tetrahydrofuran / 64 h / 20 °C

6.2: 59 percent / NaHSO₃; H₂O / tetrahydrofuran / 2.5 h / Heating

With osmium(VIII) oxide; n-butyllithium; sodium hexamethyldisilazane; Dess-Martin periodane; triethylamine; triphenylphosphine; (2-iPrO-3-PhC₆H₃CH=)(1,3-di-Mes-imidazolidin-2-ylidene)RuCl₂; In tetrahydrofuran; hexane; dichloromethane; 1.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2006.05.088

upstream raw materials:

(1S,6S)-2-(2-propen-2-yl)-9-p-toluenesulfonyl-9-azabicyclo[4.2.1]non-2-ene

(2S,5S)-5-But-3-enyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carbaldehyde

[(2S,5S)-5-But-3-enyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-methanol

(2S,5S)-5-(but-3-enyl)-2-(prop-1-ynyl)-1-p-toluenesulfonylpyrrolidine

Downstream raw materials:

(+)-N-tosylanatoxin-a