phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate

Base Information

• Chemical Name: phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate
• CAS No.: 718629-32-4
• Molecular Formula: C₂₈H₂₉Br₂NO₄Si
• Molecular Weight: 631.436

Synonyms:phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate

Chemical Property of phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate

Chemical Property:

Purity/Quality:

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Technology Process of phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate

There total 8 articles about phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-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: 77.0%

carbon tetrabromide (558-13-4) + (R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester (718629-31-3) → phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate (718629-32-4)

Guidance literature:

With triphenylphosphine; In dichloromethane; at -78 - -40 ℃;

DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propan-1-ol (213478-44-5) → phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate (718629-32-4)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine

2.1: nBu₄NI / dimethylsulfoxide

3.1: DIBAL-H / -70 °C

3.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

4.1: 100 percent / pyridine

5.1: tetrahydrofuran / -78 °C

6.1: HF / acetonitrile; H₂O / 0 °C

7.1: (COCl)2; EtN(iPr)2; DMSO / CH₂Cl₂ / 14 h / -78 °C

8.1: 77 percent / PPh₃ / CH₂Cl₂ / -78 - -40 °C

With oxalyl dichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 7.1: Swern oxidation / 8.1: Corey-Fuchs reaction;

DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

Acetic acid (S)-3-hydroxy-2-quinolin-4-yl-propyl ester (213478-42-3) → phenyl (2R)-4-[(R)-5-acetoxy-1,1-dibromopent-1-en-3-yl]-2-trimethylsilylethynyl-1,2-dihydroquinoline-1-carboxylate (718629-32-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: imidazole / dimethylformamide

2.1: KOH / methanol / 0 °C

3.1: pyridine

4.1: nBu₄NI / dimethylsulfoxide

5.1: DIBAL-H / -70 °C

5.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

6.1: 100 percent / pyridine

7.1: tetrahydrofuran / -78 °C

8.1: HF / acetonitrile; H₂O / 0 °C

9.1: (COCl)2; EtN(iPr)2; DMSO / CH₂Cl₂ / 14 h / -78 °C

10.1: 77 percent / PPh₃ / CH₂Cl₂ / -78 - -40 °C

With 1H-imidazole; potassium hydroxide; oxalyl dichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 9.1: Swern oxidation / 10.1: Corey-Fuchs reaction;

DOI:10.1016/j.tetlet.2004.04.029

upstream raw materials:

carbon tetrabromide

(R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propan-1-ol

Acetic acid (S)-3-hydroxy-2-quinolin-4-yl-propyl ester

Downstream raw materials:

phenyl (2S,3S,4R)-4-[(R)-5-[(tert-butyldimethylsilyl)oxy]-1-iodo-pent-1-yn-3-yl]-3,4-epoxy-2-iodoethynyl-3,4-dihydro-2H-quinoline-1-carboxylate

phenyl (2R)-2-ethynyl-4-[(R)-5-hydroxypent-1-yn-3-yl]-1,2-dihydroquinoline-1-carboxylate

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