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

Base Information

• Chemical Name: benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate
• CAS No.: 310404-52-5
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583
• Mol file: 310404-52-5.mol

Synonyms:benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate

Chemical Property of benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

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Technology Process of benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate

There total 4 articles about benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate 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: 69.0%

isobutene (115-11-7,15220-85-6) + benzyl hydrogen (S)-2-(tert-butyldimethylsilyloxy)succinate (309730-43-6) → benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate (310404-52-5)

Guidance literature:

With sulfuric acid; In dichloromethane; at 20 ℃;

DOI:10.1021/jo0006573

Reference yield:

(S)-3-(Benzyloxycarbonyl)-3-hydroxypropanoic acid (66178-04-9) → benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate (310404-52-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; sulfuric acid; In dichloromethane; N,N-dimethyl-formamide; 1: silylation / 2: Addition;

DOI:10.1021/jo0006573

Reference yield:

benzyl alcohol (100-51-6,185532-71-2) → benzyl tert-butyl (S)-2-(tert-butyldimethylsilyloxy)succinate (310404-52-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: TFAA / 3 h / 0 °C

1.2: 88 percent / 4 h / 20 °C

2.1: 78 percent / imidazole / dimethylformamide / 8 h / 20 °C

3.1: 69 percent / H₂SO₄ / CH₂Cl₂ / 20 °C

With 1H-imidazole; sulfuric acid; trifluoroacetic anhydride; In dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 1.2: benzylation / 2.1: silylation / 3.1: Addition;

DOI:10.1021/jo0006573

upstream raw materials:

isobutene

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

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

benzyl alcohol

Downstream raw materials:

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

benzyl tert-butyl (R)-2-phthalimidooxysuccinate