Docetaxel intermediate

Base Information

• Chemical Name: Docetaxel intermediate
• CAS No.: 114915-14-9
• Molecular Formula: C49H55Cl6NO18
• Molecular Weight: 1158.69
• Mol file: 114915-14-9.mol

Synonyms:Benzenepropanoicacid, b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxy-,12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-ylester, [2aR-[2aa,4b,4ab,6b,9a(aR*,bS*),11a,12a,12aa,12ba]]- (9CI);(2α,5β,7β,10β,13α)-4-Acetoxy-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1-hydroxy-9-oxo-7,10-bis{[(2,2,2-trichloroethoxy)carbonyl]oxy}-5,20-epoxytax-11-en-2-yl benzoate;benzenepropanoic acid, β-[[(1,1-dimethylethoxy)carbonyl]amino]-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4,6-bis[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-;

Chemical Property of Docetaxel intermediate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.607
• Boiling Point: 1064.656 °C at 760 mmHg
• PKA: 11.20±0.46(Predicted)
• Flash Point: 597.682 °C
• PSA: 224.45000
• Density: 1.503 g/cm³
• LogP: 3.65050
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

99%min ^*data from raw suppliers

7,10-O-ditrocdocetaxel 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Docetaxel intermediate

There total 37 articles about Docetaxel intermediate 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%

13-[(2'R,4'S,5'R)-3'-t-butoxycarbonyl-2'-(1'''-naphthyl)-4'-phenyl-1,3-oxazolidine-5-carbonyl]-7,10-(di-2'',2'',2''-trichloroethoxy carbonyl)-10-deacetylbaccatin III (1033962-64-9) → 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel (114915-14-9)

Guidance literature:

13-[(2'R,4'S,5'R)-3'-t-butoxycarbonyl-2'-(1'''-naphthyl)-4'-phenyl-1,3-oxazolidine-5-carbonyl]-7,10-(di-2'',2'',2''-trichloroethoxy carbonyl)-10-deacetylbaccatin III; With toluene-4-sulfonic acid; In chloroform; at 20 ℃; for 3h;

With water; sodium hydrogencarbonate; In chloroform;

Reference yield: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + 10-deacetyl-7,10-diTroc-baccatin III (114915-16-1) → 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel (114915-14-9)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(00)79128-3

Reference yield: 63.0%

di-tert-butyl dicarbonate (24424-99-5) + C44H45Cl6N3O16 (174729-13-6) → 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel (114915-14-9)

Guidance literature:

With potassium hydrogencarbonate; triphenylphosphine; In dichloromethane; water; for 19h; Ambient temperature;

DOI:10.1016/S0040-4020(98)01108-9

upstream raw materials:

di-tert-butyl dicarbonate

10-deacetyl-7,10-diTroc-baccatin III

N-chloro-N-sodio-tert-butylcarbamate

C₄₄H₄₅Cl₆N₃O₁₆

Downstream raw materials:

10-deacetyl-7,10-diTroc-baccatin III

Docetaxel

10-deacetylpaclitaxel

C₅₁H₅₁Cl₆NO₁₇

Refernces

• 1、 -. "Method for purifying docetaxel". Paragraph 0048-0050. . Retrieved 2019/07/04.
• 2、 -. "METHOD FOR PREPARING TAXANE DERIVATIVES". . . Retrieved 2012/02/15.