7-Troc-paclitaxel

Base Information

• Chemical Name: 7-Troc-paclitaxel
• CAS No.: 114915-17-2
• Molecular Formula: C50H52Cl3NO16
• Molecular Weight: 1029.32
• Mol file: 114915-17-2.mol

Synonyms:7-Troc-Paclitaxel;Paclitaxel Impurity 50;(N-1)Paxlitaxl intermediate 2;7-(2,2,2-Trichloroethyloxycarbonyl)taxol;Benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, (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-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-4-[[(2,2,2-trichloroethoxy)carbonyl]oxy]-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-...

Chemical Property of 7-Troc-paclitaxel

Chemical Property:

• Boiling Point: 1041.1±65.0 °C(Predicted)
• PKA: 11.90±0.20(Predicted)
• Density: 1.46±0.1 g/cm3(Predicted)

Purity/Quality:

95%min. ^*data from raw suppliers

7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl}Paclitaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 7-{[(2,2,2,-Trichloroethyl)oxy]carbonyl} Paclitaxel can be used as reactant/reagent for semisynthesis of taxol and Docetaxel via direct esterification of deacetylbaccatin with C13 side chain. It can also be used as reactant/reagent in synthetic preparation and reaction of anti-tumor agents.

Technology Process of 7-Troc-paclitaxel

There total 16 articles about 7-Troc-paclitaxel 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: 87.0%

benzoyl chloride (98-88-4) + C43H48Cl3NO15 (114915-15-0) → C50H52Cl3NO16 (114915-17-2)

Guidance literature:

With sodium hydrogencarbonate; In water; ethyl acetate;

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

Reference yield:

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester (144787-20-2) → C50H52Cl3NO16 (114915-17-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

2: 76 percent / NaHCO₃ / CH₂Cl₂ / 20 °C

3: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C

4: 100 percent / LiOH, H₂O / ethanol / 20 °C

5: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C

6: 80 percent / HCOOH / 4 h / 20 °C

7: 87 percent / NaHCO₃ / ethyl acetate; H₂O

With dmap; lithium hydroxide; formic acid; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; water; ethyl acetate; toluene;

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

Reference yield:

benzaldehyde (100-52-7) → C50H52Cl3NO16 (114915-17-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Et₃N, Bu₂BOTf / 1.) CH₂Cl₂, -70 to 20 deg C, 2 h, 2.) -78 to 0 deg C, 1 h

2: 81 percent / tetrahydrofuran / 0.25 h / -75 - 15 °C

3: 99 percent / NaN₃, NH₄Cl / ethanol / 8 h / 60 °C

4: 86 percent / H₂ / 10percent Pd/C / ethyl acetate / 760 Torr

5: 76 percent / NaHCO₃ / CH₂Cl₂ / 20 °C

6: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C

7: 100 percent / LiOH, H₂O / ethanol / 20 °C

8: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C

9: 80 percent / HCOOH / 4 h / 20 °C

10: 87 percent / NaHCO₃ / ethyl acetate; H₂O

With dmap; lithium hydroxide; formic acid; sodium azide; di-n-butylboryl trifluoromethanesulfonate; water; hydrogen; pyridinium p-toluenesulfonate; sodium hydrogencarbonate; ammonium chloride; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; toluene;

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

upstream raw materials:

benzoyl chloride

C₄₃H₄₈Cl₃NO₁₅

10-deacetylbaccatin III

(2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester

Downstream raw materials:

taxol

Refernces

• 1、 Mangatal,Adeline,Guenard,Gueritte-Voegelein,Potier. "Application of the vicinal oxyamination reaction with asymmetric induction to the hemisynthesis of taxol and analogues". . p. 4177 - 4190. Retrieved 2007/10/02.