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

Base Information

Chemical Name:2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel
CAS No.:618887-04-0
Molecular Formula:C₆₁H₈₀INO₁₄Si₂
Molecular Weight:1234.38
Hs Code.:

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

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

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

There total 12 articles about 2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-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: 77.0%

: 618886-93-4
(3R,4S)-1-(3-ethenylbenzoyl)-3-triethylsilyloxy-4-phenylazetidin-2-one

: 618886-91-2
7-triethylsilyl-2-debenzoyl-2-(3-iodobenzoyl)baccatin III

: 618887-04-0
2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -40 ℃; for 0.583333h;
DOI:10.1021/ol0354627

Reference yield:

: 1711-10-0
3-iodobenzoyl chloride

: 618887-04-0
2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 77 percent / Ph₃P / Pd₂(dba)3 / dioxane / 60 °C

3: 99 percent / HF*pyridine / acetonitrile; pyridine / 24 h / 0 °C

4: 93 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h

5: 77 percent / LiHMDS / tetrahydrofuran / 0.58 h / -40 °C

With dmap; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; acetonitrile; 5: Ojima-Holton β-lactam ring-opening coupling;
DOI:10.1021/ol0354627

Reference yield:

: 132127-31-2
(3R,4S)-3-triisopropylsilyloxy-4-phenylazetidin-2-one

: 618887-04-0
2-debenzoyl-2-(3-iodobenzoyl)-3'N-debenzoyl-3'N-(3-ethenylbenzoyl)-2'-triethylsilyl-7-triethylsilylpaclitaxel

Guidance literature:: Multi-step reaction with 5 steps

1: 81 percent / Et₃N / CH₂Cl₂ / 1 h / 20 °C

2: 77 percent / Ph₃P / Pd₂(dba)3 / dioxane / 60 °C

3: 99 percent / HF*pyridine / acetonitrile; pyridine / 24 h / 0 °C

4: 93 percent / DMAP; Et₃N / CH₂Cl₂ / 2 h

5: 77 percent / LiHMDS / tetrahydrofuran / 0.58 h / -40 °C

With dmap; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; acetonitrile; 5: Ojima-Holton β-lactam ring-opening coupling;
DOI:10.1021/ol0354627