Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester

Base Information

• Chemical Name: Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester
• CAS No.: 145387-85-5
• Molecular Formula: C₃₈H₅₄N₂O₉S₂Si
• Molecular Weight: 775.072

Synonyms:

Chemical Property of Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester

There total 12 articles about Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester 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:

1-(2-Methoxy-ethyl)-cyclohexa-2,5-dienecarboxylic acid (124981-58-4) → Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester (145387-85-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 1) (PhO)2P(=O)N₃, Et₃N, pyrrolidine; 2) I₂, H₂O / 2) THF

2: 2,2'-azobisisobutyronitrile / benzene / Ambient temperature

4: 4-(N,N-dimethylamino)pyridine, pyridine

6: BBr₃

7: Swern oxidation

9: 68 percent / H₂, pyridine / BaSO₄

10: 86 percent / Ph₃P, diethyl azodicarboxylate

11: (CH₃)3SiCl, NaI / acetonitrile

12: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

With pyrrolidine; pyridine; dmap; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); diphenyl phosphoryl azide; water; hydrogen; iodine; boron tribromide; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)60944-9

Reference yield:

(1R,5R,8R)-8-Iodo-1-(2-methoxy-ethyl)-6-oxa-bicyclo[3.2.1]oct-2-en-7-one (145387-74-2) → Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester (145387-85-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 2,2'-azobisisobutyronitrile / benzene / Ambient temperature

3: 4-(N,N-dimethylamino)pyridine, pyridine

5: BBr₃

6: Swern oxidation

8: 68 percent / H₂, pyridine / BaSO₄

9: 86 percent / Ph₃P, diethyl azodicarboxylate

10: (CH₃)3SiCl, NaI / acetonitrile

11: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); hydrogen; boron tribromide; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4039(00)60944-9

Reference yield:

(1S,5R,6S)-6-Allyl-5-hydroxy-1-(2-methoxy-ethyl)-cyclohex-2-enecarboxylic acid (4-methoxy-phenyl)-amide → Acetic acid (4aR,5S,8aR)-2-(4-methoxy-phenyl)-1-oxo-8a-[(Z)-(S)-8-(toluene-4-sulfonyloxy)-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester (145387-85-5)

Guidance literature:

Multi-step reaction with 9 steps

1: 4-(N,N-dimethylamino)pyridine, pyridine

3: BBr₃

4: Swern oxidation

6: 68 percent / H₂, pyridine / BaSO₄

7: 86 percent / Ph₃P, diethyl azodicarboxylate

8: (CH₃)3SiCl, NaI / acetonitrile

9: Et₃N, 4-(N,N-dimethylamino)pyridine / CH₂Cl₂

With pyridine; dmap; chloro-trimethyl-silane; hydrogen; boron tribromide; triethylamine; triphenylphosphine; sodium iodide; diethylazodicarboxylate; barium sulfate; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4039(00)60944-9

upstream raw materials:

Acetic acid (4aR,5S,8aR)-8a-[(Z)-(S)-8-hydroxy-2-(2-trimethylsilanyl-ethanesulfonylamino)-oct-3-enyl]-2-(4-methoxy-phenyl)-1-oxo-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester

p-toluenesulfonyl chloride

1-(2-Methoxy-ethyl)-cyclohexa-2,5-dienecarboxylic acid

(1R,5R,8R)-8-Iodo-1-(2-methoxy-ethyl)-6-oxa-bicyclo[3.2.1]oct-2-en-7-one

Downstream raw materials:

C₂₄H₂₈N₂O₃

Acetic acid (4aR,5S,8aR)-8a-[(Z)-(R)-1-(1,2,5,6,7,8-hexahydro-azocin-2-yl)methyl]-2-(4-methoxy-phenyl)-1-oxo-1,2,3,4,4a,5,6,8a-octahydro-isoquinolin-5-yl ester

C₂₆H₃₆N₂O₅

C₂₆H₃₄N₂O₅

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