phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

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Chemical Name:phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate
CAS No.:718629-30-2
Molecular Formula:C₃₃H₄₅NO₅Si₂
Molecular Weight:591.895
Hs Code.:

Synonyms:phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

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Chemical Property of phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

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Technology Process of phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

There total 7 articles about phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-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:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 718629-30-2
phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 7 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

With 1H-imidazole; potassium hydroxide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1016/j.tetlet.2004.04.029

Reference yield:

: Acetic acid (R)-3-(tert-butyl-dimethyl-silanyloxy)-2-quinolin-4-yl-propyl ester

: 718629-30-2
phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 6 steps

1.1: KOH / methanol / 0 °C

2.1: pyridine

3.1: nBu₄NI / dimethylsulfoxide

4.1: DIBAL-H / -70 °C

4.2: 62 percent / NaBH₄ / methanol / -40 - -10 °C

5.1: 100 percent / pyridine

6.1: tetrahydrofuran / -78 °C

With potassium hydroxide; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; methanol; dimethyl sulfoxide;
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

: 718629-30-2
phenyl (2R)-4-{(S)-4-acetoxy-1-[(tert-butyldimethylsilyl)oxy]but-2-yl}-2-[(trimethylsilyl)ethynyl]-1,2-dihydroquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 5 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

With tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; In tetrahydrofuran; pyridine; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2004.04.029