2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Base Information

• Chemical Name: 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel
• CAS No.: 618886-85-4
• Molecular Formula: C₆₁H₈₀INO₁₄Si₂
• Molecular Weight: 1234.38
• Mol file: 618886-85-4.mol

Synonyms:2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Chemical Property of 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

There total 9 articles about 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel 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: 88.0%

7-triethylsilyl-2-debenzoyl-2-(3-ethenylbenzoyl)baccatin III (436845-71-5) + (3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one (618886-87-6) → 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel (618886-85-4)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 0.666667h;

DOI:10.1021/ol0354627

Reference yield:

triethylsilyl chloride (994-30-9) → 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel (618886-85-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 82 percent / imidazole / dimethylformamide / 3 h / 0 °C

2.1: LiHMDS / tetrahydrofuran / 0.25 h / -40 °C

2.2: 83 percent / tetrahydrofuran / 2 h / -40 °C

3.1: 88 percent / LiHMDS / tetrahydrofuran / 0.67 h / -40 °C

With 1H-imidazole; lithium hexamethyldisilazane; In tetrahydrofuran; N,N-dimethyl-formamide; 3.1: Ojima-Holton β-lactam ring-opening coupling;

DOI:10.1021/ol0354627

Reference yield:

3-iodobenzoyl chloride (1711-10-0) → 2-debenzoyl-2-(3-ethenylbenzoyl)-3'N-debenzoyl-3'N-(3-iodobenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel (618886-85-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 4 h / 20 °C

2: 88 percent / LiHMDS / tetrahydrofuran / 0.67 h / -40 °C

With dmap; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 2: Ojima-Holton β-lactam ring-opening coupling;

DOI:10.1021/ol0354627

upstream raw materials:

7-triethylsilyl-2-debenzoyl-2-(3-ethenylbenzoyl)baccatin III

(3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

triethylsilyl chloride

3-iodobenzoyl chloride