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

Base Information

• Chemical Name: (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine
• CAS No.: 444789-01-9
• Molecular Formula: C₂₃H₃₇N₂O₅P
• Molecular Weight: 452.531
• Mol file: 444789-01-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine 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: 5.0%

diethyl (1-phenylethenyl)phosphonate (25944-64-3) + C11H19N2O2(1-)*Li(1+) → (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-01-9) + (2S,5R,2'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-04-2) + [4-((R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-3-(diethoxy-phosphoryl)-1,3-diphenyl-butyl]-phosphonic acid diethyl ester

Guidance literature:

diethyl (1-phenylethenyl)phosphonate; C₁₁H₁₉N₂O₂^(1-)*Li⁽¹⁺⁾; In tetrahydrofuran; at -78 ℃; for 0.0833333h;

With acetic acid; at -78 - 20 ℃;

DOI:10.1016/S0957-4166(02)00082-4

Reference yield: 3.0%

diethyl (1-phenylethenyl)phosphonate (25944-64-3) + (2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine (110117-71-0) → (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-01-9) + (2S,5R,2'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-04-2) + [4-((R)-3,6-Diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-3-(diethoxy-phosphoryl)-1,3-diphenyl-butyl]-phosphonic acid diethyl ester

Guidance literature:

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

diethyl (1-phenylethenyl)phosphonate; In tetrahydrofuran; hexane; at -78 ℃;

DOI:10.1021/jo034707q

Reference yield:

O,O-diethyl benzylphosphonate (1080-32-6) → (2S,5R,2'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-2'-phenylethyl]-2,5-dihydro-5-isopropylpyrazine (444789-01-9)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/jo034707q

upstream raw materials:

diethyl (1-phenylethenyl)phosphonate

(2R)-3,6-diethoxy-2-isopropyl-2,5-dihydropyrazine

O,O-diethyl benzylphosphonate

Downstream raw materials:

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

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

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

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