(2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid

Base Information

• Chemical Name: (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid
• CAS No.: 1333081-34-7
• Molecular Formula: C₃₉H₄₀N₂O₇
• Molecular Weight: 648.756
• Mol file: 1333081-34-7.mol

Synonyms:

Chemical Property of (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid

There total 12 articles about (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic 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:

C25H30N2O7 + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid (1333081-34-7)

Guidance literature:

With triethylamine; In water; acetonitrile; at 0 - 20 ℃; for 2h;

DOI:10.1021/jm2016914

Reference yield:

(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pent-1-en-3-ol (1361407-53-5) → (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid (1333081-34-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: pyridine; dmap / chloroform / 2 h / 0 °C

2.1: dimethylsulfide; ozone / ethyl acetate / 0.5 h / -78 - 0 °C

3.1: N-ethyl-N,N-diisopropylamine; lithium chloride / acetonitrile / 0.33 h / 0 °C / Inert atmosphere

3.2: 3 h / 0 °C / Inert atmosphere

4.1: methanol; potassium carbonate / 2 h / 0 - 20 °C

5.1: triethylamine / dichloromethane / 2 h / 0 °C

6.1: copper(l) cyanide; lithium chloride / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 - 0 °C / Inert atmosphere

7.1: fluorosilicic acid; water / acetonitrile / 2 h / 0 - 20 °C

8.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 °C / Inert atmosphere

9.1: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 3 h / 20 °C

10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

11.1: triethylamine / water; acetonitrile / 2 h / 0 - 20 °C

With pyridine; methanol; dmap; fluorosilicic acid; dimethylsulfide; water; copper(l) cyanide; potassium carbonate; ozone; thiophenol; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; chloroform; water; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 3.1: Horner-Wadsworth-Emmons olefination / 3.2: Horner-Wadsworth-Emmons olefination / 8.1: Mitsunobu reaction;

DOI:10.1021/jm2016914

Reference yield:

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-(4-methoxyphenyl)hex-2-enoate (1361407-55-7) → (2R,5R,3E)-2-{3-[N-[(benzyloxy)carbonyl]amino]propyl}-5-{N-[(9-fluorenylmethoxy)carbonyl]amino}-6-(4-methoxyphenyl)-hex-3-enoic acid (1333081-34-7)

Guidance literature:

Multi-step reaction with 7 steps

1: triethylamine / dichloromethane / 2 h / 0 °C

2: copper(l) cyanide; lithium chloride / tetrahydrofuran; diethyl ether; pentane / 1 h / -78 - 0 °C / Inert atmosphere

3: fluorosilicic acid; water / acetonitrile / 2 h / 0 - 20 °C

4: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 3 h / 0 °C / Inert atmosphere

5: potassium carbonate; thiophenol / N,N-dimethyl-formamide / 3 h / 20 °C

6: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

7: triethylamine / water; acetonitrile / 2 h / 0 - 20 °C

With fluorosilicic acid; water; copper(l) cyanide; potassium carbonate; thiophenol; triethylamine; triphenylphosphine; trifluoroacetic acid; lithium chloride; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; pentane; 4: Mitsunobu reaction;

DOI:10.1021/jm2016914

upstream raw materials:

(3R,4R)-4-[N-(tert-butoxycarbonyl)amino]-5-(4-methoxyphenyl)pent-1-en-3-ol

tert-butyl (4R,5R,2E)-4-acetoxy-5-[N-(tert-butoxycarbonyl)-amino]-6-(4-methoxyphenyl)hex-2-enoate

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-hydroxy-6-(4-methoxyphenyl)hex-2-enoate

tert-butyl (4R,5R,2E)-5-[N-(tert-butoxycarbonyl)amino]-4-[(methylsulfonyl)oxy]-6-(4-methoxyphenyl)hex-2-enoate