methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

Base Information

• Chemical Name: methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate
• CAS No.: 176703-36-9
• Molecular Formula: C₁₇H₁₉NO₆
• Molecular Weight: 333.341
• Mol file: 176703-36-9.mol

Synonyms:methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

Chemical Property of methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

There total 17 articles about methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate 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: 92.0%

methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (270086-11-8) → methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (176703-36-9)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 2h;

DOI:10.3987/com-99-s117

Reference yield:

methyl (4S,5S)-4-acetoxymethyl-5-(3-benzyloxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (176703-33-6) → methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (176703-36-9)

Guidance literature:

With aluminium trichloride; pyridinium chlorochromate; sodium iodide; Yield given. Multistep reaction;

DOI:10.1016/0040-4039(96)00430-3

Reference yield:

(2S,3SR)-2-amino-6-benzyloxy-3-hydroxyhexanoic acid (189071-56-5) → methyl (4S,5S)-4-acetoxymethyl-5-(2-formylethyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (176703-36-9)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine / CH₂Cl₂ / 0.5 h / 0 °C

2: 30 mg / diethyl ether; methanol / 0 °C

3: 1N HCl / methanol / 4 h / 60 °C

4: H₂O; diethyl ether / 19 h / 20 °C

5: DBU / dimethylformamide / 1 h / 20 °C

6: pyridine / 20 °C

7: 88 percent / aluminum chloride; sodium iodide / acetonitrile / 2.5 h / 20 °C

8: 92 percent / pyridinium chlorochromate / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; aluminium trichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; pyridinium chlorochromate; sodium iodide; In pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Acetylation / 2: Methylation / 3: Hydrolysis / 4: Cycloaddition / 5: hydroxymethylation / 6: Acetylation / 7: dealkylation / 8: Oxidation;

DOI:10.3987/com-99-s117

upstream raw materials:

methyl (4S,5S)-4-acetoxymethyl-5-(3-benzyloxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

benzoic acid anhydride

(2S,3SR)-2-amino-6-benzyloxy-3-hydroxyhexanoic acid

Downstream raw materials:

methyl (4S,5S)-4-acetoxymethyl-5-[(3E)-11,11-ethylenedioxyheptadec-3-enyl]-2-phenyl-Δ²-oxazoline-4-carboxylate

(2S,3S)-(E)-2-amino-3-hydroxy-2-hydroxymethyl-14-oxoicos-6-enoic acid

methyl (4S,5S)-4-acetoxymethyl-5-[(3Z)-11,11-ethylenedioxyheptadec-3-enyl]-2-phenyl-Δ²-oxazoline-4-carboxylate