(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone

Base Information

• Chemical Name: (4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone
• CAS No.: 189013-31-8
• Molecular Formula: C₂₇H₂₈N₂O₄S
• Molecular Weight: 476.596
• Mol file: 189013-31-8.mol

Synonyms:(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone

Chemical Property of (4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone

There total 1 articles about (4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone 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: 89.0%

4-(benzyloxy)benzoic acid chloride (1486-50-6) + 3-[(4-methylphenyl)sulfonyl]perhydro-azireno[2,3-c]azepine (164738-24-3) → (4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone (189013-31-8)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1016/S0040-4020(97)00167-1

Reference yield: 82.0%

(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone (189013-31-8) → (3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide (189013-33-0)

Guidance literature:

With water; toluene-4-sulfonic acid; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1016/S0040-4020(97)00167-1

Reference yield:

(4-Benzyloxy-phenyl)-[(1R,7S)-3-(toluene-4-sulfonyl)-3,8-diaza-bicyclo[5.1.0]oct-8-yl]-methanone (189013-31-8) → balanol

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / water; p-toluenesulfonic acid / tetrahydrofuran / 6 h / 20 °C

2: 90 percent / 2-chloro-1-methylpyridinium iodide; triethylamine; DMAP / CH₂Cl₂ / 3.5 h

3: Na₂HPO₄; sodium amalgam / methanol / 6 h / Heating

4: 0.0021 g / HCO₂H / Pd black

With dmap; disodium hydrogenphosphate; sodium amalgam; formic acid; 2-chloro-1-methyl-pyridinium iodide; water; toluene-4-sulfonic acid; triethylamine; palladium; In tetrahydrofuran; methanol; dichloromethane; 1: Ring cleavage / 2: Mukaiyama esterification / 3: detosylation / 4: debenzylation;

DOI:10.1016/S0040-4020(97)00167-1

upstream raw materials:

4-(benzyloxy)benzoic acid chloride

3-[(4-methylphenyl)sulfonyl]perhydro-azireno[2,3-c]azepine

Downstream raw materials:

(3R,4R)-4-benzyloxy-N-[4-hydroxy-1-(toluene-4-sulfonyl)-azepan-3-yl]-benzamide

3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-3-(4-benzyloxy-benzoylamino)-azepan-4-yl ester

3,5-Bis-benzyloxy-4-(2-benzyloxy-6-benzyloxycarbonyl-benzoyl)-benzoic acid (3R,4R)-3-(4-benzyloxy-benzoylamino)-1-(toluene-4-sulfonyl)-azepan-4-yl ester