Azidotaxol

Base Information

• Chemical Name: Azidotaxol
• CAS No.: 153695-19-3
• Molecular Formula: C47H50 N4 O14
• Molecular Weight: 894.9183
• Nikkaji Number: J588.727E
• ChEMBL ID: CHEMBL307603
• Mol file: 153695-19-3.mol

Synonyms:3'-(4-azidobenzamido)taxol;AzB-taxol;azidotaxol;N-((3,5-(3)H)-4-azidobenzoyl)-N-debenzoyltaxol;N-(4-azidobenzoyl)-N-debenzoyltaxol

Chemical Property of Azidotaxol

Chemical Property:

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 271.04000
• Density: g/cm³
• LogP: 4.52116
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 15
• Exact Mass: 894.33235228
• Heavy Atom Count: 65
• Complexity: 1970

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=C(C=C6)N=[N+]=[N-])O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=C(C=C6)N=[N+]=[N-])O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C

Technology Process of Azidotaxol

There total 13 articles about Azidotaxol 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: 79.0%

4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0) + 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6) → N-(4-azidobenzoyl)-N-debenzoyltaxol (153695-19-3)

Guidance literature:

With pyridine; dmap; for 1h;

DOI:10.1021/jm00036a009

Reference yield: 79.0%

C2HF3O2*C40H47NO13 + 4-azidobenzoic acid N-hydroxysuccinimide ester (53053-08-0) → N-(4-azidobenzoyl)-N-debenzoyltaxol (153695-19-3)

Guidance literature:

Reference yield: 72.0%

4-azidobenzoyl chloride (14848-01-2) + 13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6) → N-(4-azidobenzoyl)-N-debenzoyltaxol (153695-19-3)

Guidance literature:

With sodium hydrogencarbonate; In ethyl acetate; for 0.0833333h;

upstream raw materials:

4-azidobenzoic acid N-hydroxysuccinimide ester

13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III

4-azidobenzoyl chloride

C₆₂H₈₄N₄O₁₄Si₂

Refernces

• 1、 -. "Synthesis of taxol, analogs and intermediates with variable A-nng side chains". Page 8-9, 17. . Retrieved 2010/01/31.
• 2、 Dasgupta,Park,Harriman,Georg,Himes. "Synthesis of a photoaffinity taxol analogue and its use in labeling tubulin". . p. 2976 - 2980. Retrieved 2007/10/02.