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

Base Information

• Chemical Name: (3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one
• CAS No.: 618886-87-6
• Molecular Formula: C₂₂H₂₆INO₃Si
• Molecular Weight: 507.443
• Mol file: 618886-87-6.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one 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%

3-iodobenzoyl chloride (1711-10-0) + (3R,4S)-3-triethylsilyloxy-4-phenylazetidin-2-one (149140-54-5) → (3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one (618886-87-6)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 4h;

DOI:10.1021/ol0354627

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:

(3R,4S)-1-(3-iodobenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one (618886-87-6) → C49H51NO14

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / LiHMDS / tetrahydrofuran / 0.67 h / -40 °C

2: AsPh₃; Et₃N / Pd₂(dba)3 / acetonitrile / 24 h / 55 °C

3: 4 mg / HF*pyridine / acetonitrile; pyridine

With triphenyl-arsane; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; pyridine; acetonitrile; 1: Ojima-Holton β-lactam ring-opening coupling / 2: intramolecular Heck reaction;

DOI:10.1021/ol0354627

upstream raw materials:

3-iodobenzoyl chloride

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

Downstream raw materials:

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