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

Base Information

• Chemical Name: methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ²-oxazoline-4-carboxylate
• CAS No.: 270086-11-8
• Molecular Formula: C₁₇H₂₁NO₆
• Molecular Weight: 335.357

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

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

Chemical Property:

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

There total 14 articles about methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-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: 88.0%

methyl (4S,5S)-4-acetoxymethyl-5-(3-benzyloxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (176703-33-6) → methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (270086-11-8)

Guidance literature:

With aluminium trichloride; sodium iodide; In acetonitrile; at 20 ℃; for 2.5h;

DOI:10.3987/com-99-s117

Reference yield:

(2S,3SR)-2-amino-6-benzyloxy-3-hydroxyhexanoic acid (189071-56-5) → methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (270086-11-8)

Guidance literature:

Multi-step reaction with 7 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

With hydrogenchloride; aluminium trichloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; 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;

DOI:10.3987/com-99-s117

Reference yield:

(S)-2-Acetylamino-6-benzyloxy-3-hydroxy-hexanoic acid → methyl (4S,5S)-4-acetoxymethyl-5-(3-hydroxypropyl)-2-phenyl-Δ2-oxazoline-4-carboxylate (270086-11-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 30 mg / diethyl ether; methanol / 0 °C

2: 1N HCl / methanol / 4 h / 60 °C

3: H₂O; diethyl ether / 19 h / 20 °C

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

5: pyridine / 20 °C

6: 88 percent / aluminum chloride; sodium iodide / acetonitrile / 2.5 h / 20 °C

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

DOI:10.3987/com-99-s117

upstream raw materials:

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

benzoic acid anhydride

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

methyl (2S,3S)-2-acetamido-6-benzyloxy-3-hydroxyhexanoate

Downstream raw materials:

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

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-(2-formylethyl)-2-phenyl-Δ²-oxazoline-4-carboxylate

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