(R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester

Base Information

• Chemical Name: (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester
• CAS No.: 326473-67-0
• Molecular Formula: C₄₄H₆₆N₄O₈Si
• Molecular Weight: 807.116
• Mol file: 326473-67-0.mol

Synonyms:

Chemical Property of (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester

There total 6 articles about (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl 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:

(R)-2-[2-(Diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester + (2-{(S)-3-Methyl-1-[(E)-(1S,2R)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enylcarbamoyl]-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester → (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester (326473-67-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In dichloromethane; acetonitrile; at 20 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(00)00766-3

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester (326473-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 °C

2.1: 10 percent HCl / methanol / 2 h

2.2: 77 percent / EDCI*HCl; DMAP / CH₂Cl₂ / 2 h / 0 °C

3.1: Dess-Martin periodinate / CH₂Cl₂ / 0.5 h / 20 °C

4.1: LiCl; DBU / acetonitrile; CH₂Cl₂ / 0.17 h / 20 °C

With hydrogenchloride; dmap; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium chloride; In methanol; dichloromethane; acetonitrile; 1.1: Condensation / 2.1: Hydrolysis / 2.2: Condensation / 3.1: Oxidation / 4.1: Horner-Emmons reaction;

DOI:10.1016/S0040-4020(00)00766-3

Reference yield:

(E)-(1S,2R)-1-(2-Methoxymethoxy-ethyl)-2-methyl-4-phenyl-but-3-enylamine (326473-57-8) → (R)-2-{(2E,7E)-(5S,6R)-5-[(S)-2-(3-tert-Butoxycarbonylamino-propionylamino)-4-methyl-pentanoylamino]-6-methyl-8-phenyl-octa-2,7-dienoylamino}-3-(4-methoxy-phenyl)-propionic acid 2-trimethylsilanyl-ethyl ester (326473-67-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / DCC; DMAP / CH₂Cl₂ / 2 h / 0 °C

2.1: 10 percent HCl / methanol / 2 h

2.2: 77 percent / EDCI*HCl; DMAP / CH₂Cl₂ / 2 h / 0 °C

3.1: Dess-Martin periodinate / CH₂Cl₂ / 0.5 h / 20 °C

4.1: LiCl; DBU / acetonitrile; CH₂Cl₂ / 0.17 h / 20 °C

With hydrogenchloride; dmap; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; lithium chloride; In methanol; dichloromethane; acetonitrile; 1.1: Condensation / 2.1: Hydrolysis / 2.2: Condensation / 3.1: Oxidation / 4.1: Horner-Emmons reaction;

DOI:10.1016/S0040-4020(00)00766-3

upstream raw materials:

N-tert-butoxycarbonyl-L-leucine

(E)-(1S,2R)-1-(2-Methoxymethoxy-ethyl)-2-methyl-4-phenyl-but-3-enylamine

{(S)-1-[(E)-(1S,2R)-1-(2-Methoxymethoxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butyl}-carbamic acid tert-butyl ester

(2-{(S)-1-[(E)-(1S,2R)-1-(2-Hydroxy-ethyl)-2-methyl-4-phenyl-but-3-enylcarbamoyl]-3-methyl-butylcarbamoyl}-ethyl)-carbamic acid tert-butyl ester