(S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS No.: 855526-97-5
• Molecular Formula: C₃₈H₅₅NO₆
• Molecular Weight: 621.858
• Mol file: 855526-97-5.mol

Synonyms:(S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property of (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

There total 7 articles about (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 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: 73.0%

(S)-4-((E)-(R)-1-Methoxymethoxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-96-4) + (4-bromophenyl)(phenyl)methanone (90-90-4) → (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-97-5)

Guidance literature:

(S)-4-((E)-(R)-1-Methoxymethoxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; at 20 ℃;

(4-bromophenyl)(phenyl)methanone; With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; water; at 85 ℃;

DOI:10.1021/jo050513u

Reference yield:

dodec-11-en-1-ynyl-trimethyl-silane → (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-97-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 0.67 g / NaOH / diethyl ether; H₂O / 1 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: 76 percent / HMPA / tetrahydrofuran; hexane / 2.5 h / -78 °C

3.1: 58 percent / Red-Al / diethyl ether; toluene / 4.17 h / 0 - 20 °C

4.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

5.1: 9-BBN-H / tetrahydrofuran / 20 °C

5.2: 73 percent / Pd(PPh₃)4; K₃PO₄ / tetrahydrofuran; dioxane; H₂O / 85 °C

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; 5.2: Suzuki coupling;

DOI:10.1021/jo050513u

Reference yield:

(S)-4-((E)-(R)-1-Hydroxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-95-3) → (S)-4-[(E)-(R)-13-(4-Benzoyl-phenyl)-1-methoxymethoxy-tridec-2-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-97-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

2.1: 9-BBN-H / tetrahydrofuran / 20 °C

2.2: 73 percent / Pd(PPh₃)4; K₃PO₄ / tetrahydrofuran; dioxane; H₂O / 85 °C

With 9-borabicyclo[3.3.1]nonane dimer; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; 2.2: Suzuki coupling;

DOI:10.1021/jo050513u

upstream raw materials:

(S)-4-((E)-(R)-1-Methoxymethoxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(4-bromophenyl)(phenyl)methanone

(S)-4-((E)-(R)-1-Hydroxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-4-((R)-1-Hydroxy-tridec-12-en-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Downstream raw materials:

(2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

(2S,3R)-1-O-[(2'-aminoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

(2S,3R)-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol