{3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester

Base Information

• Chemical Name: {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester
• CAS No.: 204513-85-9
• Molecular Formula: C₃₉H₆₂N₂O₆Si
• Molecular Weight: 683.017
• Mol file: 204513-85-9.mol

Synonyms:{3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester

Chemical Property of {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester

There total 9 articles about {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl 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:

(S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester (79677-60-4) → {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester (204513-85-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Heating

2: Et₃N, (PPh₃)2PdCl₂, CuI / acetonitrile / 4 h / Ambient temperature

3: H₂, AcOH / 5percent Pd/C / methanol / 16 h / 2585.7 Torr

4: N-methylmorpholine / CH₂Cl₂ / 16 h / Ambient temperature

5: 1 M LiOH / tetrahydrofuran / 1.5 h / Ambient temperature

6: BH₃ / tetrahydrofuran / 2 h / -5 - 10 °C

7: imidazole, N-methylmorpholine / acetonitrile / 2.5 h / 60 °C

With 4-methyl-morpholine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; borane; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm980001q

Reference yield:

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride (79677-58-0,122908-62-7) → {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester (204513-85-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) N-methylmorpholine / 1.) CH₂Cl₂, 15 min, 2.) CH₂Cl₂, from 10 deg C to RT, 3 h

2: 60 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / Heating

3: Et₃N, (PPh₃)2PdCl₂, CuI / acetonitrile / 4 h / Ambient temperature

4: H₂, AcOH / 5percent Pd/C / methanol / 16 h / 2585.7 Torr

5: N-methylmorpholine / CH₂Cl₂ / 16 h / Ambient temperature

6: 1 M LiOH / tetrahydrofuran / 1.5 h / Ambient temperature

7: BH₃ / tetrahydrofuran / 2 h / -5 - 10 °C

8: imidazole, N-methylmorpholine / acetonitrile / 2.5 h / 60 °C

With 4-methyl-morpholine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; borane; tetrabutyl ammonium fluoride; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm980001q

Reference yield:

(S)-2-Benzyloxycarbonylamino-3-[4-(2-cyclohexyl-ethoxy)-3-iodo-phenyl]-propionic acid methyl ester (204513-78-0) → {3-[5-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester (204513-85-9)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N, (PPh₃)2PdCl₂, CuI / acetonitrile / 4 h / Ambient temperature

2: H₂, AcOH / 5percent Pd/C / methanol / 16 h / 2585.7 Torr

3: N-methylmorpholine / CH₂Cl₂ / 16 h / Ambient temperature

4: 1 M LiOH / tetrahydrofuran / 1.5 h / Ambient temperature

5: BH₃ / tetrahydrofuran / 2 h / -5 - 10 °C

6: imidazole, N-methylmorpholine / acetonitrile / 2.5 h / 60 °C

With 4-methyl-morpholine; 1H-imidazole; bis-triphenylphosphine-palladium(II) chloride; lithium hydroxide; copper(l) iodide; borane; hydrogen; acetic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;

DOI:10.1021/jm980001q

upstream raw materials:

tert-butyldimethylsilyl chloride

N-(Benzyloxycarbonyloxy)succinimide

(S)-N-benzyloxycarbonyl-3-(4-hydroxy-3-iodophenyl)alanine methyl ester

2-amino-3-(3-iodo-4-hydroxyphenyl)propionic acid methyl ester hydrochloride

Downstream raw materials:

{3-[5-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propyl]-2-(2-cyclohexyl-ethoxy)-phenyl]-propyl}-carbamic acid tert-butyl ester