(2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine

Base Information

• Chemical Name: (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine
• CAS No.: 911319-51-2
• Molecular Formula: C₃₃H₄₂N₂O₅Si
• Molecular Weight: 574.792
• Mol file: 911319-51-2.mol

Synonyms:(2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine

Chemical Property of (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine

There total 23 articles about (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine 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: 90.0%

Benzoic acid (E)-4-{(2S,3S)-3-hydroxy-2-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-piperidin-1-yl}-but-2-enyl ester (911319-71-6) → (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine (911319-51-2)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.75h;

DOI:10.1021/ol061524s

Reference yield:

(2R,3R)-2-tert-Butoxycarbonylamino-3-(6-methoxy-quinolin-4-yl)-3-triethylsilanyloxy-propionic acid methyl ester (911319-44-3) → (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine (911319-51-2)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 81 percent / DIBAL-H / toluene; hexane / -78 °C

2.1: Mg; I₂ / diethyl ether / 1 h / 20 °C

2.2: 87 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

3.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

4.1: DIBAL-H / tetrahydrofuran; hexane / -78 - 0 °C

5.1: 100 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

6.1: 82 percent / H₂ / Pd/C / methanol; ethyl acetate / 24 h / 20 °C / atmospheric pressure

7.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

8.1: 99 percent / NaH / tetrahydrofuran / 2 h / 20 °C

9.1: 94 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

11.1: 93 percent / K₂CO₃; Et₃N / dimethylformamide / 24 h / 20 °C

12.1: aq. HCl / tetrahydrofuran / 1 h / 0 °C

13.1: 90 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.75 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol061524s

Reference yield:

(2R,3R)-2-tert-butoxycarbonylamino-3-(6-methoxyquinol-4-yl)-3-triethylsilyloxy-propanal (911319-65-8) → (2R)-1-[(E)-4-benzoyloxy-2-butenyl]-2-[(R)-6-methoxyquinol-4-yl-triethylsilyloxy]methyl-3-oxo-piperidine (911319-51-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Mg; I₂ / diethyl ether / 1 h / 20 °C

1.2: 87 percent / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C

2.1: 85 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

3.1: DIBAL-H / tetrahydrofuran; hexane / -78 - 0 °C

4.1: 100 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

5.1: 82 percent / H₂ / Pd/C / methanol; ethyl acetate / 24 h / 20 °C / atmospheric pressure

6.1: 94 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

7.1: 99 percent / NaH / tetrahydrofuran / 2 h / 20 °C

8.1: 94 percent / LiAlH₄ / diethyl ether / 0.17 h / 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

10.1: 93 percent / K₂CO₃; Et₃N / dimethylformamide / 24 h / 20 °C

11.1: aq. HCl / tetrahydrofuran / 1 h / 0 °C

12.1: 90 percent / (COCl)2; DMSO / CH₂Cl₂ / 0.75 h / -78 °C

With 2,6-dimethylpyridine; hydrogenchloride; dmap; lithium aluminium tetrahydride; oxalyl dichloride; hydrogen; iodine; sodium hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/ol061524s

upstream raw materials:

Benzoic acid (E)-4-{(2S,3S)-3-hydroxy-2-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-piperidin-1-yl}-but-2-enyl ester

trans-1-iodo-4-benzoyloxy-2-butene

(2R,3R)-2-tert-butoxycarbonylamino-3-(6-methoxyquinol-4-yl)-3-triethylsilyloxy-propanal

(2R,3R)-2-tert-Butoxycarbonylamino-3-(6-methoxy-quinolin-4-yl)-3-triethylsilanyloxy-propionic acid methyl ester

Downstream raw materials:

(R)-1-((E)-4-Benzoyloxy-but-2-enyl)-2-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-3-oxo-piperidine-4-carboxylic acid methyl ester

Benzoic acid (E)-4-{(R)-6-[(R)-(6-methoxy-quinolin-4-yl)-triethylsilanyloxy-methyl]-5-trimethylsilanyloxy-3,6-dihydro-2H-pyridin-1-yl}-but-2-enyl ester