Taxol C

Base Information

• Chemical Name: Taxol C
• CAS No.: 153415-45-3
• Molecular Formula: C46H57 N O14
• Molecular Weight: 847.957
• European Community (EC) Number: 630-574-3
• UNII: L5P3TE6LS8
• DSSTox Substance ID: DTXSID00433334
• Nikkaji Number: J598.521H
• Metabolomics Workbench ID: 130137
• ChEMBL ID: CHEMBL306601
• Mol file: 153415-45-3.mol

Synonyms:Taxol C;153415-45-3;Paclitaxel C;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;L5P3TE6LS8;SCHEMBL44876;CHEMBL306601;DTXSID00433334;AKOS040762410;HY-137776;PACLITAXEL IMPURITY C [EP IMPURITY];CS-0141878;7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv;4,10beta-bis(acetyloxy)-13alpha-[[(2R,3S)-3-(hexanoylamino)-2-hydroxy-3-phenylpropanoyl]oxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate (N-debenzoyl-N-hexanoylpaclitaxel;Benzenepropanoic acid, alpha-hydroxy-beta-[(1-oxohexyl)amino]-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-;Benzenepropanoic acid, alpha-hydroxy-beta-[(1-oxohexyl)amino]-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha]]-

Chemical Property of Taxol C

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 932.3°Cat760mmHg
• PKA: 11.93±0.20(Predicted)
• Flash Point: 517.6°C
• PSA: 224.78000
• Density: 1.34g/cm³
• LogP: 4.84250
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 17
• Exact Mass: 847.37790549
• Heavy Atom Count: 61
• Complexity: 1730

Purity/Quality:

99% ^*data from raw suppliers

PaclitaxelC ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)NC(C1=CC=CC=C1)C(C(=O)OC2CC3(C(C4C(C(CC5C4(CO5)OC(=O)C)O)(C(=O)C(C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• Isomeric SMILES: CCCCCC(=O)N[C@@H](C1=CC=CC=C1)[C@H](C(=O)O[C@H]2C[C@]3([C@H]([C@H]4[C@@]([C@H](C[C@@H]5[C@]4(CO5)OC(=O)C)O)(C(=O)[C@@H](C(=C2C)C3(C)C)OC(=O)C)C)OC(=O)C6=CC=CC=C6)O)O
• Uses: Paclitaxel related compound C. Paclitaxel analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to Paclitaxel. Paclitaxel related compound C. Paclitaxel analogs were tested for tubulin assembly and cytotoxicity, and were shown to retain potency similar to Paclitaxel. Paclitaxel EP Impurity C.

Technology Process of Taxol C

There total 2 articles about Taxol C 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: 56.0%

13-(O-2R-hydroxy-3S-amine-phenylpropionyl)-baccatin III (133524-70-6) + hexanoic acid (142-62-1) → taxuyunnansine (153415-45-3)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

DOI:10.1021/jm049344g

Reference yield:

3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel (602319-12-0) → taxuyunnansine (153415-45-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / zinc; AcOH / ethyl acetate / 8 h

2: 56 percent / 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride; 1-hydroxybenzotriazole / dimethylformamide / 3 h / 20 °C

With benzotriazol-1-ol; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm049344g

Reference yield: 87.0%

tert-butyldimethylsilyl chloride (18162-48-6) + taxuyunnansine (153415-45-3) → C52H71NO14Si (876716-86-8)

Guidance literature:

With 1H-imidazole; In dichloromethane;

DOI:10.1016/j.bmcl.2005.10.063

upstream raw materials:

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

hexanoic acid

3'-N-debenzoyl-3'-N-Troc-7-Troc-paclitaxel

Downstream raw materials:

C₅₂H₇₁NO₁₄Si

C₅₀H₆₉NO₁₃Si

C₅₆H₈₃NO₁₃Si₂

C₅₆H₈₃NO₁₃Si₂