(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

Base Information

• Chemical Name: (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid
• CAS No.: 179093-50-6
• Molecular Formula: C₂₅H₃₇ClN₂O₈
• Molecular Weight: 529.03
• Mol file: 179093-50-6.mol

Synonyms:(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

Chemical Property of (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

There total 15 articles about (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid 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: 90.0%

(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid allyl ester (182486-23-3) → (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid (179093-50-6)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 23 ℃; for 1h;

DOI:10.1021/jo960972i

Reference yield: 84.0%

benzyl (2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(3-chloro-4-methoxyphenyl) propionylamino]-2-methylpropionyloxy]-4-methylpentanoate (196794-47-5) → (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid (179093-50-6)

Guidance literature:

With hydrogen; Ra-Ni;

DOI:10.1021/jo971645t

Reference yield:

(R)-2-((tet-butoxycarbonyl)amino)-3-(3-chloro-4-methoxyphenyl)propanoic acid (162465-45-4) → (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid (179093-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 87.5 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

2: hydrogen / Pd(OH)2 on carbon / ethyl acetate / 2 h / 20 °C

With N-[3-(diethylamino)propyl]-N'-ethylcarbodiimide hydrochloride; hydrogen; benzotriazol-1-ol; triethylamine; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: coupling / 2: Hydrogenolysis;

DOI:10.1021/jo9907585

upstream raw materials:

(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid allyl ester

(S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid

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

di-tert-butyl dicarbonate

Downstream raw materials:

(2E,7E)-(S)-5-((S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(3-chloro-4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoyloxy)-6-oxo-8-phenyl-octa-2,7-dienoic acid tert-butyl ester

(E)-(3S,6R,10R,16S)-10-(3-Chloro-4-methoxy-benzyl)-16-((1R,2R,3R)-2,3-dihydroxy-1-methyl-3-phenyl-propyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

(E)-(3S,6R,10R,16S)-16-((1R,2R,3R)-3-Chloro-2-hydroxy-1-methyl-3-phenyl-propyl)-10-(3-chloro-4-methoxy-benzyl)-3-isobutyl-6-methyl-1,4-dioxa-8,11-diaza-cyclohexadec-13-ene-2,5,9,12-tetraone

cryptophycin C