ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

Base Information

• Chemical Name: ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate
• CAS No.: 618893-41-7
• Molecular Formula: C₂₁H₃₄NO₇P
• Molecular Weight: 443.477
• Mol file: 618893-41-7.mol

Synonyms:ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

Chemical Property of ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate

There total 4 articles about ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate 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: 95.0%

di-tert-butyl dicarbonate (24424-99-5) + ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate (444789-52-0) → ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate (618893-41-7)

Guidance literature:

With sodium hydrogencarbonate; sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 7h;

DOI:10.1021/jo034707q

Reference yield:

diethyl (1-phenylethenyl)phosphonate (25944-64-3) → ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate (618893-41-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

2.1: 92 percent / HCl / tetrahydrofuran / 12 h / 20 °C

3.1: 95 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 7 h / 0 - 20 °C

With hydrogenchloride; n-butyllithium; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; hexane; water;

DOI:10.1021/jo034707q

Reference yield:

(2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-01-9) → ethyl (2S,4R)-2-[(tert-butoxycarbonyl)amino]-4-(diethoxyphosphoryl)-4-phenylbutanoate (618893-41-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / HCl / tetrahydrofuran / 12 h / 20 °C

2: 95 percent / Na₂CO₃; NaHCO₃ / dioxane; H₂O / 7 h / 0 - 20 °C

With hydrogenchloride; sodium hydrogencarbonate; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; water;

DOI:10.1021/jo034707q

upstream raw materials:

di-tert-butyl dicarbonate

ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate

O,O-diethyl benzylphosphonate

diethyl (1-phenylethenyl)phosphonate

Downstream raw materials:

((3S,5S)-2-Ethoxy-2-oxo-3-phenyl-2λ⁵-[1,2]oxaphosphinan-5-yl)-carbamic acid tert-butyl ester

(3R,5S)-5-[(tert-butoxycarbonyl)amino]-2-ethoxy-3-phenyl-2-oxo-1,2-oxaphosphorinane