benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate

Base Information

• Chemical Name: benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate
• CAS No.: 728032-81-3
• Molecular Formula: C₃₁H₄₁ClN₂O₈
• Molecular Weight: 605.128
• Mol file: 728032-81-3.mol

Synonyms:benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate

Chemical Property of benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate

There total 5 articles about benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate 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-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate (728032-81-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / K₂CO₃; tetrabutylammonium iodide / dimethylformamide / 1.5 h / 20 °C

2: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

3: TFA / CH₂Cl₂ / 3.5 h / 20 °C

4: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

With dmap; tetra-(n-butyl)ammonium iodide; potassium carbonate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm030555f

Reference yield:

(R)-2-(3-Amino-propionyloxy)-4-methyl-pentanoic acid benzyl ester (697217-20-2) + (R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (162465-45-4) → benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate (728032-81-3)

Guidance literature:

With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 0 - 20 ℃; for 16.5h;

DOI:10.1021/jm030555f

Reference yield:

benzyl (R)-2-hydroxy-4-methylpentanoate (37755-48-9) → benzyl (2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoate (728032-81-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / DMAP; DCC / CH₂Cl₂ / 19.5 h / 0 - 20 °C

2: TFA / CH₂Cl₂ / 3.5 h / 20 °C

3: 0.63 g / HOBT; DIEA; DCC / tetrahydrofuran / 16.5 h / 0 - 20 °C

With dmap; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm030555f

upstream raw materials:

(R)-2-(3-Amino-propionyloxy)-4-methyl-pentanoic acid benzyl ester

(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid

(R)-2-hydroxy-4-methylpentanoic acid

benzyl (R)-2-hydroxy-4-methylpentanoate

Downstream raw materials:

(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoic acid

6-demethyldesepoxy-3-epicryptophycin-1

tert-butyl (5S,6R)-5-[(2R)-2-[3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl)propionylamino]propionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate