3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester
• CAS No.: 642087-17-0
• Molecular Formula: C₂₉H₃₆ClNO₅
• Molecular Weight: 514.062
• Mol file: 642087-17-0.mol

Synonyms:

Chemical Property of 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester

There total 5 articles about 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic 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:

Acetic acid (E)-(1S,2R)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester + 3-(diethoxyphosphinyl)-N-(3-chloro-4-methoxyphenyl)-D-alanine tert-butyl ester (642087-13-6) → 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester (642087-17-0)

Guidance literature:

3-(diethoxyphosphinyl)-N-(3-chloro-4-methoxyphenyl)-D-alanine tert-butyl ester; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 1h;

Acetic acid (E)-(1S,2R)-2-methyl-1-(2-oxo-ethyl)-4-phenyl-but-3-enyl ester; In tetrahydrofuran; for 1.5h;

DOI:10.1021/jo035077v

Reference yield:

(R)-tert-butyl 2-amino-3-(4-methoxyphenyl)propionate (281190-95-2) → 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester (642087-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 96 percent / DCC / tetrahydrofuran / 1 h / 23 °C

2.1: KCl; oxone / acetonitrile; H₂O / 5 h / 23 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 109 mg / tetrahydrofuran / 1.5 h

With Oxone; potassium chloride; sodium hydride; dicyclohexyl-carbodiimide; In tetrahydrofuran; water; acetonitrile; 3.2: Horner-Emmons reaction;

DOI:10.1021/jo035077v

Reference yield:

ethyl 2-((3R,5S)-3-methyl-5-phenyltetrahydrofuran-2-yl)acetate → 3-(3-chloro-4-methoxyphenyl)-(2R)-2-((5S,6R)-5-hydroxy-6-methyl-8-phenyl-octa-2(E),7(E)-dienoylamino)propionic acid tert-butyl ester (642087-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / ZnCl₂ / 8.5 h / 120 °C

2.1: DIBAL-H / CH₂Cl₂; hexane / 1.17 h / -78 °C

3.1: NaH / tetrahydrofuran / 1 h / 0 °C

3.2: 109 mg / tetrahydrofuran / 1.5 h

With sodium hydride; diisobutylaluminium hydride; zinc(II) chloride; In tetrahydrofuran; hexane; dichloromethane; 3.2: Horner-Emmons reaction;

DOI:10.1021/jo035077v

upstream raw materials:

3-(diethoxyphosphinyl)-N-(3-chloro-4-methoxyphenyl)-D-alanine tert-butyl ester

(R)-tert-butyl 2-amino-3-(4-methoxyphenyl)propionate

ethyl (3S,4R)-3-acetoxy-4-methyl-6-phenylhexan-(5E)-oate

2-[2-(diethoxy-phosphoryl)-acetylamino]-3-(4-methoxy-phenyl)-propionic acid tert-butyl ester

Downstream raw materials:

(S)-2-(3-Amino-2,2-dimethyl-propionyloxy)-4-methyl-pentanoic acid (E)-(1S,2R)-1-{(E)-3-[(R)-1-carboxy-2-(3-chloro-4-methoxy-phenyl)-ethylcarbamoyl]-allyl}-2-methyl-4-phenyl-but-3-enyl ester

cryptophycin 53

cryptophycin 52

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