(1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester

Base Information

• Chemical Name: (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester
• CAS No.: 618892-44-7
• Molecular Formula: C₁₄H₂₁O₄P
• Molecular Weight: 284.292
• Mol file: 618892-44-7.mol

Synonyms:(1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester

Chemical Property of (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester

There total 2 articles about (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester 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:

Diethyl phosphonate (762-04-9,123-22-8) + ((Z)-3-Bromo-allyloxymethyl)-benzene → (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester (618892-44-7)

Guidance literature:

With triethylamine; In toluene; at 90 ℃; for 1.5h;

DOI:10.1021/jo034707q

Reference yield:

1,1-dibromo-3-benzyloxy-1-propene (149125-65-5) → (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester (618892-44-7)

Guidance literature:

Multi-step reaction with 2 steps

1: Bu₃SnH; Pd(PPh₃)4 / toluene / 1.5 h / 70 °C

2: Et₃N / toluene / 1.5 h / 90 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tri-n-butyl-tin hydride; triethylamine; In toluene;

DOI:10.1021/jo034707q

Reference yield: 15.0%

(3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine (134870-62-5) + (1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester (618892-44-7) → (2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (618892-48-1) + (2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine (182207-35-8) + [5-Benzyloxy-2-benzyloxymethyl-4-((S)-3,6-diethoxy-5-isopropyl-2,5-dihydro-pyrazin-2-yl)-3-(diethoxy-phosphoryl)-pentyl]-phosphonic acid diethyl ester

Guidance literature:

(3S)-3,6-dihydro-2,5-diethoxy-3-isopropylpyrazine; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

(1Z)-[3-(benzyloxy)-1-propenyl]phosphonic acid diethyl ester; In tetrahydrofuran; hexane; at -78 ℃; for 0.0833333h;

DOI:10.1021/jo034707q

upstream raw materials:

Diethyl phosphonate

1,1-dibromo-3-benzyloxy-1-propene

Downstream raw materials:

(2R,5S,1'S)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine

(2R,5S,1'R)-3,6-diethoxy-2-[2'-(diethoxyphosphoryl)-1'-(benzyloxymethyl)ethyl]-2,5-dihydro-5-isopropylpyrazine