(S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Base Information

• Chemical Name: (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester
• CAS No.: 439589-27-2
• Molecular Formula: C₄₁H₅₆N₂O₆S
• Molecular Weight: 704.971
• Mol file: 439589-27-2.mol

Synonyms:(S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property of (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

There total 10 articles about (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-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: 61.0%

(S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-19-2) → (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-27-2) + (R)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

Guidance literature:

With caesium carbonate; In acetonitrile; at 20 ℃; for 240h;

DOI:10.1021/jo025571j

Reference yield:

(+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-hydroxybicyclo[2.2.1]heptane-1-methanesulfonamide (99295-72-4) → (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 1551.49 Torr

3.1: methanol / 2 h / 20 °C

3.2: NaBH₃CN; ZnCl₂ / methanol / 2 h / 20 °C

4.1: 94 percent / propylene oxide / tetrahydrofuran / 20 °C

5.1: 55 percent / BTPP / CH₂Cl₂ / 24 h / 20 °C

With dmap; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo025571j

Reference yield:

benzyl (S)-(1-fluoro-1-oxo-3-phenylpropan-2-yl)carbamate (133010-22-7) → (S)-2-Benzyl-1-(4-methoxy-benzyl)-4-oxo-azetidine-2-carboxylic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester (439589-27-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / DMAP / CH₂Cl₂ / 1 h / 20 °C

2.1: H₂ / Pd/C / methanol / 1 h / 20 °C / 1551.49 Torr

3.1: methanol / 2 h / 20 °C

3.2: NaBH₃CN; ZnCl₂ / methanol / 2 h / 20 °C

4.1: 94 percent / propylene oxide / tetrahydrofuran / 20 °C

5.1: 55 percent / BTPP / CH₂Cl₂ / 24 h / 20 °C

With dmap; hydrogen; tert-butylimino-tri(pyrrolidino)phosphorane; methyloxirane; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo025571j

upstream raw materials:

(S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-3-phenyl-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(+)-(1R,2S,4S)-N,N-dicyclohexyl-7,7-dimethyl-2-hydroxybicyclo[2.2.1]heptane-1-methanesulfonamide

benzyl (S)-(1-fluoro-1-oxo-3-phenylpropan-2-yl)carbamate

2-(4-methoxy-benzylamino)-3-phenyl-propionic acid tert-butyl ester

Downstream raw materials:

(S)-α-benzylaspartic acid

(S)-2-(4-Methoxy-benzylamino)-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(S)-2-Benzyloxycarbonylamino-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester

(S)-2-[(2-Chloro-acetyl)-(4-methoxy-benzyl)-amino]-propionic acid (1R,2S,4S)-1-[(dicyclohexylsulfamoyl)-methyl]-7,7-dimethyl-bicyclo[2.2.1]hept-2-yl ester