5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄

Base Information

• Chemical Name: 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄
• CAS No.: 190143-65-8
• Molecular Formula: C₄₅H₆₂F₂O₉Si
• Molecular Weight: 813.064
• Mol file: 190143-65-8.mol

Synonyms:5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄

Chemical Property of 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄

There total 5 articles about 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A₄ 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:

tert-butyldimethylsilyl chloride (18162-48-6) → 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A4 (190143-65-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaBH₄, 2) imidazole / 1) MeOH, 0 deg C, 20 min, 2) DMF, room temperature, 2 h

2: 89 percent / n-BuNH₂, PPh₃, formic acid / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / Ambient temperature

3: 66 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; formic acid; N-butylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb.61.806

Reference yield:

30-Hydroxymilbemycin A4 (123022-52-6) → 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A4 (190143-65-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 81 percent / MnO₂ / CH₂Cl₂ / 3 h / Ambient temperature

2: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

3: 1) NaBH₄, 2) imidazole / 1) MeOH, 0 deg C, 20 min, 2) DMF, room temperature, 2 h

4: 89 percent / n-BuNH₂, PPh₃, formic acid / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / Ambient temperature

5: 66 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; manganese(IV) oxide; sodium tetrahydroborate; formic acid; N-butylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb.61.806

Reference yield:

5-deoxy-24a-hydroxy-5-oxomilbemycin A4 (141547-99-1) → 5-O-t-butyldimethylsilyl-24a-(2,6-difluorobenzoyloxy)milbemycin A4 (190143-65-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

2: 1) NaBH₄, 2) imidazole / 1) MeOH, 0 deg C, 20 min, 2) DMF, room temperature, 2 h

3: 89 percent / n-BuNH₂, PPh₃, formic acid / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / Ambient temperature

4: 66 percent / pyridine / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 1H-imidazole; sodium tetrahydroborate; formic acid; N-butylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane;

DOI:10.1271/bbb.61.806

upstream raw materials:

tert-butyldimethylsilyl chloride

30-Hydroxymilbemycin A₄

5-deoxy-24a-hydroxy-5-oxomilbemycin A₄

24a-allyloxycarbonyloxy-5-O-t-butyldimethylsilylmilbemycin A₄