(R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Base Information

• Chemical Name: (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester
• CAS No.: 221007-40-5
• Molecular Formula: C₄₀H₅₅NO₃Si
• Molecular Weight: 625.967
• Mol file: 221007-40-5.mol

Synonyms:

Chemical Property of (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

There total 1 articles about (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl 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:

4-methoxy-3-(trisopropylsilyl)pyridine (126378-42-5) + (1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl chloroformate (161693-64-7) + C10H9BrMg (221007-35-8) → (R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (221007-40-5) + (S)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

Guidance literature:

With oxalic acid; Yield given; Multistep reaction. Yields of byproduct given; 2.) THF,toluene, -78 deg C;

DOI:10.1016/S0040-4039(98)02273-4

Reference yield:

(R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (221007-40-5) → (2S,3S)-3-Methyl-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-piperidin-4-one (221007-57-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaOMe, 2.) aq. oxalic acid / 1.) MeOH

2: 98 percent / TEA, DMAP

3: 98 percent / NaHMDS / tetrahydrofuran / -20 °C

4: L-Selectride

5: TMSCl, NaI

With dmap; chloro-trimethyl-silane; TEA; sodium methylate; sodium hexamethyldisilazane; oxalic acid; L-Selectride; sodium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)02273-4

Reference yield:

(R)-4-Oxo-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-5-triisopropylsilanyl-3,4-dihydro-2H-pyridine-1-carboxylic acid (1S,2R)-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester (221007-40-5) → (-)-(2S,3S,4R)-dienomycin C

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaOMe, 2.) aq. oxalic acid / 1.) MeOH

2: 98 percent / TEA, DMAP

3: 98 percent / NaHMDS / tetrahydrofuran / -20 °C

4: L-Selectride

5: TMSCl, NaI

6: 83 percent / L-Selectride

With dmap; chloro-trimethyl-silane; TEA; sodium methylate; sodium hexamethyldisilazane; oxalic acid; L-Selectride; sodium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(98)02273-4

upstream raw materials:

4-methoxy-3-(trisopropylsilyl)pyridine

(1S,2R)-2-(1-methyl-1-phenylethyl)cyclohexyl chloroformate

C₁₀H₉BrMg

Downstream raw materials:

(1S,2R)-(+)-trans-2-(1-methyl-1-phenylethyl)cyclohexanol

(R)-2-((1E,3E)-4-Phenyl-buta-1,3-dienyl)-2,3-dihydro-1H-pyridin-4-one

(2S,3S)-3-Methyl-2-((1E,3E)-4-phenyl-buta-1,3-dienyl)-piperidin-4-one

4-oxo-2-(4-phenyl-buta-1,3-dienyl)-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester