(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

Base Information

• Chemical Name: (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane
• CAS No.: 1220994-31-9
• Molecular Formula: C₁₉H₂₀O₂
• Molecular Weight: 280.367
• Mol file: 1220994-31-9.mol

Synonyms:(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

Chemical Property of (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane

There total 8 articles about (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane 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:

C26H28O5S → (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane (1220994-31-9)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.1002/hlca.200900170

Reference yield:

(2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol (1220994-32-0) → (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane (1220994-31-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

1.2: 6.17 h / 0 - 20 °C / Inert atmosphere

2.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

3.1: dmap; triethylamine / dichloromethane / 1 h / Inert atmosphere

4.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

With dmap; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/cjoc.201190015

Reference yield:

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol (914638-76-9) → (2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]oxirane (1220994-31-9)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(l) iodide; palladium 10% on activated carbon; potassium carbonate; triphenylphosphine / 1,2-dimethoxyethane; water / 0.5 h / 20 °C / Inert atmosphere

1.2: 5 h / 85 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 0 °C

3.1: sodium hydride / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

3.2: 6.17 h / 0 - 20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C / Inert atmosphere

5.1: dmap; triethylamine / dichloromethane / 1 h / Inert atmosphere

6.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; lithium aluminium tetrahydride; palladium 10% on activated carbon; pyridinium p-toluenesulfonate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; water;

DOI:10.1002/cjoc.201190015

upstream raw materials:

(S)-(S)-1-(1,4-Dioxa-spiro[4.5]dec-2-yl)-but-3-yn-2-ol

(2S,3E)-1-[(2S)-1,4-dioxaspiro[4.5]dec-2-yl]-4-phenyl-3-buten-2-ol

(2S)-2-[(2S,3E)-2-(benzyloxy)-4-phenylbut-3-en-1-yl]-1,4-dioxaspiro[4.5]decane

(2S,4S,5E)-4-(benzyloxy)-6-phenylhex-5-ene-1,2-diol

Downstream raw materials:

(αR,2S)-α-(2-phenylethyl)oxirane-2-ethanol

(4R,6S,7E)-6-(benzyloxy)-8-phenylocta-1,7-dien-4-ol

tert-butyl((1R,5R,7S,8E)-5,7-di(benzyloxy)-9-phenyl-1-[2-(tetrahydro-2H-2-pyranyloxy)ethyl]-8-nonen-2-ynyloxy)dimethylsilane

(3R,7R,9S,10E)-7,9-di(benzyloxy)-11-phenyl-1-(tetrahydro-2H-2-pyranyloxy)-10-undecen-4-yn-3-ol