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

Base Information

Chemical Name:(R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester
CAS No.:718629-31-3
Molecular Formula:C₂₇H₂₉NO₅Si
Molecular Weight:475.616
Hs Code.:

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

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

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

There total 8 articles about (R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl 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:

: phenyl (2R)-4-[(S)-4-acetoxy-1-(hydroxy)but-2-yl]-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

: 718629-31-3
(R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 14h;
DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

: 213478-44-5
(R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propan-1-ol

: 718629-31-3
(R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 7 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

With oxalyl dichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; water; dimethyl sulfoxide; acetonitrile; 7.1: Swern oxidation;
DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

: 213478-42-3
Acetic acid (S)-3-hydroxy-2-quinolin-4-yl-propyl ester

: 718629-31-3
(R)-4-((S)-3-Acetoxy-1-formyl-propyl)-2-trimethylsilanylethynyl-2H-quinoline-1-carboxylic acid phenyl ester

Guidance literature:: Multi-step reaction with 9 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

With 1H-imidazole; potassium hydroxide; oxalyl dichloride; hydrogen fluoride; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 9.1: Swern oxidation;
DOI:10.1016/j.tetlet.2004.04.029