diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate

Base Information

• Chemical Name: diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate
• CAS No.: 1449782-74-4
• Molecular Formula: C₂₈H₃₁O₄P
• Molecular Weight: 462.525
• Mol file: 1449782-74-4.mol

Synonyms:diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate

Chemical Property of diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate

There total 5 articles about diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate 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:

C26H27O4P + triethyloxonium fluoroborate (368-39-8) → diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate (1449782-74-4)

Guidance literature:

C₂₆H₂₇O₄P; With sodium hydride; In tetrahydrofuran; mineral oil; at 60 ℃; for 1h;

triethyloxonium fluoroborate; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; diastereoselective reaction;

DOI:10.1021/ol4020078

Reference yield:

butyl 2-(trityloxy)acetate (1449782-41-5) → diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate (1449782-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0.33 h / -78 °C

1.2: -78 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / tetrahydrofuran / 1 h / 60 °C

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 60 °C

4.2: 0 - 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; cyclohexane; mineral oil;

DOI:10.1021/ol4020078

Reference yield:

trityl chloride (76-83-5) → diethyl (1Z,3E)-5-(trityloxy)penta-1,3-dienylphosphonate (1449782-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: pyridine / 18 h / 65 °C

2.1: diisobutylaluminium hydride / dichloromethane; cyclohexane / 0.33 h / -78 °C

2.2: -78 - 20 °C

3.1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 0 - 20 °C

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / tetrahydrofuran / 1 h / 60 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 60 °C

5.2: 0 - 20 °C

With pyridine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; sodium hydride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; cyclohexane; mineral oil;

DOI:10.1021/ol4020078

upstream raw materials:

trityl chloride

butyl 2-(trityloxy)acetate

1-triphenylmethoxy-but-3-en-2-ol

triethyloxonium fluoroborate