(R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline

Base Information

• Chemical Name: (R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline
• CAS No.: 150884-66-5
• Molecular Formula: C₁₂H₁₄N₂O₃
• Molecular Weight: 234.255
• Mol file: 150884-66-5.mol

Synonyms:(R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline

Chemical Property of (R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline

There total 8 articles about (R)-3-benzyloxy-4-acetylamino-Δ²-isoxazoline 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: 93.0%

acetyl chloride (75-36-5) + (R)-3-benzyloxy-4-amino-Δ2-isoxazoline (150884-64-3) → (R)-3-benzyloxy-4-acetylamino-Δ2-isoxazoline (150884-66-5)

Guidance literature:

With triethylamine; In diethyl ether; at 0 ℃; for 0.5h;

DOI:10.1016/S0957-4166(00)80156-1

Reference yield:

lithium benzyloxide (15082-42-5) → (R)-3-benzyloxy-4-acetylamino-Δ2-isoxazoline (150884-66-5)

Guidance literature:

Multi-step reaction with 8 steps

1: 69 percent / dimethylsulfoxide; hexane / Ambient temperature

2: 86 percent / methanol / Ambient temperature; Amberlite IR-120

3: 81 percent / CH₂Cl₂ / 0.5 h / 0 °C

5: 90 percent / 20percent aq. potassium carbonate / methanol / 2 h / Ambient temperature

6: 73 percent / triphenylphosphine, diethylazodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 0.25 h / 0 °C

7: 1.) triphenylphosphine, 2.) water / 1.) THF, RT, 3 h, 2.) THF, RT, overnight

8: 93 percent / triethylamine / diethyl ether / 0.5 h / 0 °C

With diphenylphosphoranyl azide; water; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1016/S0957-4166(00)80156-1

Reference yield:

(R,S)-3-benzyloxy-4-hydroxy-Δ2-isoxazoline tetrahydropyranyl ether → (R)-3-benzyloxy-4-acetylamino-Δ2-isoxazoline (150884-66-5)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / methanol / Ambient temperature; Amberlite IR-120

2: 81 percent / CH₂Cl₂ / 0.5 h / 0 °C

4: 90 percent / 20percent aq. potassium carbonate / methanol / 2 h / Ambient temperature

5: 73 percent / triphenylphosphine, diethylazodicarboxylate, diphenylphosphoryl azide / tetrahydrofuran / 0.25 h / 0 °C

6: 1.) triphenylphosphine, 2.) water / 1.) THF, RT, 3 h, 2.) THF, RT, overnight

7: 93 percent / triethylamine / diethyl ether / 0.5 h / 0 °C

With diphenylphosphoranyl azide; water; potassium carbonate; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0957-4166(00)80156-1

upstream raw materials:

acetyl chloride

(R)-3-benzyloxy-4-amino-Δ²-isoxazoline

lithium benzyloxide

3-Benzyloxy-4,5-dihydro-isoxazol-4-ol

Downstream raw materials:

N-acetyl-D-cycloserine