ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate

Base Information

• Chemical Name: ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate
• CAS No.: 478623-17-5
• Molecular Formula: C₁₉H₂₇NO₅
• Molecular Weight: 349.427
• Mol file: 478623-17-5.mol

Synonyms:ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate

Chemical Property of ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate

There total 3 articles about ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate 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:

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester (94790-24-6) → ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate (478623-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / LiBH₄ / diethyl ether; methanol / 5 h / Heating

2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -45 - 0 °C

3: 1.35 g / benzene / 15 h / 20 °C

With lithium borohydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane; benzene; 2: Swern oxidation / 3: Wittig reaction;

DOI:10.1055/s-2002-33904

Reference yield:

(2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol (120349-75-9) → ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate (478623-17-5)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.25 h / -45 - 0 °C

2: 1.35 g / benzene / 15 h / 20 °C

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; benzene; 1: Swern oxidation / 2: Wittig reaction;

DOI:10.1055/s-2002-33904

Reference yield:

[(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (139183-60-1,120349-76-0) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → ethyl (2E,4R)-4-(tert-butoxycarbonyl)amino-5-(4-methoxyphenyl)pent-2-enoate (478623-17-5)

Guidance literature:

In benzene; at 20 ℃; for 15h;

DOI:10.1055/s-2002-33904

upstream raw materials:

[(R)-1-Formyl-2-(4-methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester

ethyl (triphenylphosphoranylidene)acetate

(2R)-tert-butoxycarbonylamino-3-(4-methoxyphenyl)propionic acid methyl ester

(2R)-2-(tert-butoxycarbonyl)amino-3-(4-methoxyphenyl)propan-1-ol

Downstream raw materials:

ethyl (1R,4R,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolane-4-carboxylate

(1R,4R,5R)-1-[N-(tert-butoxycarbonyl)]-1-(5-bromomethyl-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(4-methoxyphenyl)ethan-1-amine

(1R,4S,5R)-5-[1-(tert-butoxycarbonyl)amino-2-(4-methoxyphenyl)ethyl]-2,2-dimethyl-1,3-dioxolan-4-ylmethanol

(2R,3S,4S)-3,4-dihydroxy-2-(4-methoxybenzyl)pyrrolidine