2’-carboxybenzoylpaclitaxel

Base Information

• Chemical Name: 2’-carboxybenzoylpaclitaxel
• CAS No.: 148930-30-7
• Molecular Formula: C₅₅H₅₇NO₁₆
• Molecular Weight: 988.055
• Mol file: 148930-30-7.mol

Synonyms:2’-carboxybenzoylpaclitaxel

Chemical Property of 2’-carboxybenzoylpaclitaxel

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2’-carboxybenzoylpaclitaxel

There total 13 articles about 2’-carboxybenzoylpaclitaxel 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: 99.0%

taxol (33069-62-4) + benzyl chloroformate (501-53-1,94274-21-2) → 2’-carboxybenzoylpaclitaxel (148930-30-7)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/S0040-4020(01)80381-1

Reference yield: 68.0%

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + taxol (33069-62-4) → 2’-carboxybenzoylpaclitaxel (148930-30-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1016/j.bmc.2007.04.029

Reference yield:

7-O-(triethylsilyl)paclitaxel (148930-55-6) → 2’-carboxybenzoylpaclitaxel (148930-30-7)

Guidance literature:

Multi-step reaction with 6 steps

1: benzoyl peroxide

2: HCl / acetonitrile

3: N-iodosuccinimide, 4 Angstroem sieves / CH₂Cl₂; tetrahydrofuran

4: H₂ / Pd-C / ethyl acetate / 2.5 h / 3102.9 Torr / Ambient temperature

5: bovine intestinal alkaline phosphatase

6: 93 percent / iPr₂EtN / CH₂Cl₂

With hydrogenchloride; N-iodo-succinimide; 4 A molecular sieve; hydrogen; N-ethyl-N,N-diisopropylamine; dibenzoyl peroxide; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; ethyl acetate; acetonitrile;

DOI:10.1016/0960-894X(96)00321-6

upstream raw materials:

taxol

benzyl chloroformate

N-(Benzyloxycarbonyloxy)succinimide

7-O-(triethylsilyl)paclitaxel

Downstream raw materials:

C₅₇H₆₁NO₁₆S

2'-Z-7-Z-gly-paclitaxel

taxol

7-O-(triethylsilyl)paclitaxel

Refernces

• 1、 Efthimiadou, Eleni K.,Katsarou, Maria E.,Fardis, Michael,Zikos, Christos,Pitsinos, Emmanuel N.,Kazantzis, Athanasios,Leondiadis, Leondios,Sagnou, Marina,Vourloumis, Dionisios. "Synthesis and characterization of novel natural product-Gd(III) MRI contrast agent conjugates". scheme or table. p. 6058 - 6061. Retrieved 2009/07/18.
• 2、 Kumar, Srinivas K.,Williams, Simon A.,Isaacs, John T.,Denmeade, Samuel R.,Khan, Saeed R.. "Modulating paclitaxel bioavailability for targeting prostate cancer". . p. 4973 - 4984. Retrieved 2008/03/13.