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

Base Information

• Chemical Name: tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate
• CAS No.: 245125-92-2
• Molecular Formula: C₄₄H₆₂N₂O₁₀
• Molecular Weight: 778.984
• Mol file: 245125-92-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 31 articles about tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate 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: 84.0%

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate (178977-57-6) + (S)-2-{(R)-3-[(R)-2-tert-Butoxycarbonylamino-3-(4-methoxy-phenyl)-propionylamino]-2-methyl-propionyloxy}-4-methyl-pentanoic acid (179093-49-3) → tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (245125-92-2)

Guidance literature:

With dmap; diisopropyl-carbodiimide; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1021/jo9907585

Reference yield:

(S)-2-((R)-3-Amino-2-methyl-propionyloxy)-4-methyl-pentanoic acid benzyl ester (245125-89-7) → tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (245125-92-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 178.3 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

3: 84 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH₂Cl₂ / 18 h / 20 °C

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

DOI:10.1021/jo9907585

Reference yield:

(2S,2'R)-benzyl 2-[(3'-{[(tert-butoxy)carbonyl]amino}-2'-methylpropinoyl)oxy]-4-methylpentanoate (245125-88-6) → tert-butyl (5S,6R)-5-[(2S)-2-[(2R)-3-[(2R)-2-tert-butoxycarbonylamino-3-(4-methoxyphenyl)-propionylamino]-2-methylpropionyloxy]-4-methylpentanoyloxy]-6-methyl-8-phenylocta-2(E),7(E)-dienoate (245125-92-2)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / CH₂Cl₂ / 1 h / 0 °C

2: 178.3 mg / 1-hydroxybenzotriazole; triethylamine; 1-(3-diethylaminopropyl)-3-ethylcarbodiimide hydrochloride / tetrahydrofuran; CH₂Cl₂ / 0 - 20 °C

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

4: 84 percent / 4-(dimethylamino)pyridine; 1,3-diisopropylcarbodiimide / CH₂Cl₂ / 18 h / 20 °C

With dmap; N-[3-(diethylamino)propyl]-N'-ethylcarbodiimide hydrochloride; hydrogen; benzotriazol-1-ol; triethylamine; trifluoroacetic acid; diisopropyl-carbodiimide; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; ethyl acetate; 1: Hydrolysis / 2: coupling / 3: Hydrogenolysis / 4: Esterification;

DOI:10.1021/jo9907585

upstream raw materials:

tert-butyl (5S,6R,2E,7E)-5-hydroxy-6-methyl-8-phenyl-2,7-octadienoate

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

O,O-diethyl benzylphosphonate

(tert-Butoxycarbonylmethylene)triphenylphosphorane

Downstream raw materials:

Cryptophycin 4

Refernces

• 1、 Rej, Rabindra,Nguyen, Dieu,Go, Brian,Fortin, Samuel,Lavallee, Jean-Francois. "Total synthesis of cryptophycins and their 16-(3-phenylacryloyl) derivatives". . p. 6289 - 6295. Retrieved 2007/10/03.