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

Base Information

• Chemical Name: ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate
• CAS No.: 444789-52-0
• Molecular Formula: C₁₆H₂₆NO₅P
• Molecular Weight: 343.36
• Mol file: 444789-52-0.mol

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

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

There total 3 articles about ethyl (2S,4R)-2-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: 92.0%

(2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-01-9) → ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate (444789-52-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo034707q

Reference yield:

diethyl (1-phenylethenyl)phosphonate (25944-64-3) → ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate (444789-52-0)

Guidance literature:

Multi-step reaction with 2 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

With hydrogenchloride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1021/jo034707q

Reference yield:

O,O-diethyl benzylphosphonate (1080-32-6) → ethyl (2S,4R)-2-amino-4-(diethoxyphosphoryl)-4-phenylbutanoate (444789-52-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA; (EtO)2P(O)Cl / tetrahydrofuran

1.2: tetrahydrofuran

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

2.2: tetrahydrofuran; hexane / -78 °C

3.1: 92 percent / HCl / tetrahydrofuran / 12 h / 20 °C

With hydrogenchloride; n-butyllithium; diethyl chlorophosphate; lithium diisopropyl amide; In tetrahydrofuran; hexane; 1.2: Wadsworth-Emmons olefination;

DOI:10.1021/jo034707q

upstream raw materials:

(2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine

O,O-diethyl benzylphosphonate

diethyl (1-phenylethenyl)phosphonate

Downstream raw materials:

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

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

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