benzyl tert-butyl (R)-2-phthalimidooxysuccinate

Base Information

• Chemical Name: benzyl tert-butyl (R)-2-phthalimidooxysuccinate
• CAS No.: 310404-53-6
• Molecular Formula: C₂₃H₂₃NO₇
• Molecular Weight: 425.438
• Mol file: 310404-53-6.mol

Synonyms:benzyl tert-butyl (R)-2-phthalimidooxysuccinate

Chemical Property of benzyl tert-butyl (R)-2-phthalimidooxysuccinate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

Technology Process of benzyl tert-butyl (R)-2-phthalimidooxysuccinate

There total 5 articles about benzyl tert-butyl (R)-2-phthalimidooxysuccinate 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: 97.0%

N-hydroxyphthalimide (524-38-9) + 2-hydroxy-succinic acid 1-benzyl ester 4-tert-butyl ester (310404-54-7) → benzyl tert-butyl (R)-2-phthalimidooxysuccinate (310404-53-6)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In dichloromethane; at -20 ℃; for 0.5h;

DOI:10.1021/jo0006573

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → benzyl tert-butyl (R)-2-phthalimidooxysuccinate (310404-53-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / imidazole / dimethylformamide / 8 h / 20 °C

2: 69 percent / H₂SO₄ / CH₂Cl₂ / 20 °C

3: 92 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

4: 97 percent / PPh₃; DIAD / CH₂Cl₂ / 0.5 h / -20 °C

With 1H-imidazole; di-isopropyl azodicarboxylate; sulfuric acid; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Addition / 3: desilylation / 4: Substitution;

DOI:10.1021/jo0006573

Reference yield:

benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6) → benzyl tert-butyl (R)-2-phthalimidooxysuccinate (310404-53-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 69 percent / H₂SO₄ / CH₂Cl₂ / 20 °C

2: 92 percent / TBAF / tetrahydrofuran / 0.17 h / 20 °C

3: 97 percent / PPh₃; DIAD / CH₂Cl₂ / 0.5 h / -20 °C

With di-isopropyl azodicarboxylate; sulfuric acid; tetrabutyl ammonium fluoride; triphenylphosphine; In tetrahydrofuran; dichloromethane; 1: Addition / 2: desilylation / 3: Substitution;

DOI:10.1021/jo0006573

upstream raw materials:

N-hydroxyphthalimide

2-hydroxy-succinic acid 1-benzyl ester 4-tert-butyl ester

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid

benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate