(1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

Base Information

• Chemical Name: (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate
• CAS No.: 476358-99-3
• Molecular Formula: C₁₃H₁₇O₆P
• Molecular Weight: 300.248
• Mol file: 476358-99-3.mol

Synonyms:(1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

Chemical Property of (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

There total 4 articles about (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate 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: 85.0%

methyl chloroformate (79-22-1) + (R)-(+)-(1-Hydroxy-3-phenyl-2E-propenyl)phosphonic acid dimethyl ester (162681-26-7) → (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate (476358-99-3)

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; Inert atmosphere; Cooling with ice;

DOI:10.1055/s-0035-1560487

Reference yield:

styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + dimethyl [1-(methoxycarbonyloxy)-2-propenyl] phosphonate (180294-79-5) → (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate (476358-99-3) + (1S)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; copper(l) iodide; In dichloromethane; at 40 ℃; for 20h; Inert atmosphere; Reflux;

DOI:10.1055/s-0035-1560487

Reference yield:

(E)-3-phenylpropenal (14371-10-9) + methyl chloroformate (79-22-1) + Dimethyl phosphite (868-85-9) → (1R)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate (476358-99-3) + (1S)(2E) dimethyl [1-(methoxycarbonyloxy)-3-phenyl-2-propenyl] phosphonate

Guidance literature:

(E)-3-phenylpropenal; With titanium(IV) isopropylate; Dimethyl D-tartrate; In tetrahydrofuran; at -15 ℃; for 0.25h;

Dimethyl phosphite; In tetrahydrofuran; at -15 ℃;

methyl chloroformate; With pyridine; dmap; In dichloromethane; at 0 - 20 ℃; Title compound not separated from byproducts;

DOI:10.1021/jo035795h

upstream raw materials:

methyl chloroformate

(R)-(+)-(1-Hydroxy-3-phenyl-2E-propenyl)phosphonic acid dimethyl ester

(E)-3-phenylpropenal

Dimethyl phosphite