114915-17-2

Basic information

• Product Name: 7-Troc-paclitaxel
• Synonyms: 7-(2,2,2-Trichloroethyloxycarbonyl)taxol;7-Troc-Paclitaxel;(N-1)Paxlitaxl intermediate 2
• CAS NO: 114915-17-2
• Molecular Formula: C₅₀H₅₂Cl₃NO₁₆
• Molecular Weight: 1029.30398
• Product Categories: API
• Mol File: 114915-17-2.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 1041.1±65.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• PKA: 11.90±0.20(Predicted)
• CAS DataBase Reference: 7-Troc-paclitaxel(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Troc-paclitaxel(114915-17-2)
• EPA Substance Registry System: 7-Troc-paclitaxel(114915-17-2)

Safety Data

• Hazardous Substances Data: 114915-17-2(Hazardous Substances Data)

Usage

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.

Synthetic route

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

Conditions	Yield
With sodium hydrogencarbonate In water; ethyl acetate	87%
In pyridine for 3h; Ambient temperature;

10-deacetylbaccatin III (32981-86-5) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 71 percent / pyridine / 0.5 h / 80 °C 2: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 3: 80 percent / HCOOH / 4 h / 20 °C 4: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

(2R,3S)-3-amino-2-hydroxy-3-phenylpropionic acid ethyl ester (143615-00-3) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 6 steps 1: 76 percent / NaHCO3 / CH2Cl2 / 20 °C 2: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C 3: 100 percent / LiOH, H2O / ethanol / 20 °C 4: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 5: 80 percent / HCOOH / 4 h / 20 °C 6: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

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

Conditions	Yield
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 View Scheme

7-(2,2,2-trichloroethyloxycarbonyl)baccatin III (103150-33-0) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 2: 80 percent / HCOOH / 4 h / 20 °C 3: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme
Multi-step reaction with 4 steps 1: 95 percent / dicyclohexylcarbodiimide, 4-dimethyl-aminopyridine, / 15 h / 70 °C 2: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 3: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 4: pyridine / 3 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 95 percent / dicyclohexylcarbodiimide, 4-dimethyl-aminopyridine, / 15 h / 70 °C 2: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 3: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 4: pyridine / 3 h / Ambient temperature View Scheme

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

Conditions

Yield

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 View Scheme

7-triethylsilyl-10-deacetylbaccatin III (115437-18-8) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 67 percent / 0.1N HCl / ethanol / 24 h / 0 °C 2: 71 percent / pyridine / 0.5 h / 80 °C 3: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 4: 80 percent / HCOOH / 4 h / 20 °C 5: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate (126060-73-9) → C50H52Cl3NO16 (114915-17-2)

Conditions

Yield

Multi-step reaction with 8 steps 1: 99 percent / NaN3, NH4Cl / ethanol / 8 h / 60 °C 2: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 760 Torr 3: 76 percent / NaHCO3 / CH2Cl2 / 20 °C 4: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C 5: 100 percent / LiOH, H2O / ethanol / 20 °C 6: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 7: 80 percent / HCOOH / 4 h / 20 °C 8: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

(2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine (143527-75-7) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C 2: 100 percent / LiOH, H2O / ethanol / 20 °C 3: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 4: 80 percent / HCOOH / 4 h / 20 °C 5: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid (143615-03-6, 143527-70-2) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 2: 80 percent / HCOOH / 4 h / 20 °C 3: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate (143527-74-6) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 100 percent / LiOH, H2O / ethanol / 20 °C 2: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 3: 80 percent / HCOOH / 4 h / 20 °C 4: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

(4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one (144704-63-2) → C50H52Cl3NO16 (114915-17-2)

Conditions

Yield

Multi-step reaction with 9 steps 1: 81 percent / tetrahydrofuran / 0.25 h / -75 - 15 °C 2: 99 percent / NaN3, NH4Cl / ethanol / 8 h / 60 °C 3: 86 percent / H2 / 10percent Pd/C / ethyl acetate / 760 Torr 4: 76 percent / NaHCO3 / CH2Cl2 / 20 °C 5: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C 6: 100 percent / LiOH, H2O / ethanol / 20 °C 7: 99 percent / DCC, DMAP / toluene / 2 h / 80 °C 8: 80 percent / HCOOH / 4 h / 20 °C 9: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

C51H60Cl3NO17 (143527-73-5) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / HCOOH / 4 h / 20 °C 2: 87 percent / NaHCO3 / ethyl acetate; H2O View Scheme

(E)-3-phenylacrylic acid (140-10-3) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: 95 percent / dicyclohexylcarbodiimide, 4-dimethyl-aminopyridine, / 15 h / 70 °C 2: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 3: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 4: pyridine / 3 h / Ambient temperature View Scheme
Multi-step reaction with 4 steps 1: 95 percent / dicyclohexylcarbodiimide, 4-dimethyl-aminopyridine, / 15 h / 70 °C 2: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 3: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 4: pyridine / 3 h / Ambient temperature View Scheme

7(2,2,2-trichloroethyloxycarbonyl)-13-cinnamoyl baccatin III. (114915-24-1) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 2: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 3: pyridine / 3 h / Ambient temperature View Scheme
Multi-step reaction with 3 steps 1: AgNO3, OsO4, / acetonitrile; 2-methyl-propan-2-ol / 24 h / Ambient temperature 2: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 3: pyridine / 3 h / Ambient temperature View Scheme

C48H56Cl3NO17 (114915-13-8) → C50H52Cl3NO16 (114915-17-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: ISi(CH3)3 / acetonitrile / 0.5 h / 0 °C 2: pyridine / 3 h / Ambient temperature View Scheme

C50H52Cl3NO16 (114915-17-2) → taxol (33069-62-4)

Conditions	Yield
With acetic acid; zinc In methanol at 60℃; for 1h;	89%
With acetic acid; zinc In methanol at 60℃; for 2h; Yield given;

Upstream product

• 98-88-4 benzoyl chloride 
• 114915-15-0 C₄₃H₄₈Cl₃NO₁₅ 
• 32981-86-5 10-deacetylbaccatin III 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 103150-33-0 7-(2,2,2-trichloroethyloxycarbonyl)baccatin III 
• 114915-13-8 C₄₈H₅₆Cl₃NO₁₇ 
• 114915-24-1 7(2,2,2-trichloroethyloxycarbonyl)-13-cinnamoyl baccatin III_. 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 115437-18-8 7-triethylsilyl-10-deacetylbaccatin III 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 143527-73-5 C₅₁H₆₀Cl₃NO₁₇ 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 

Downstream Products

• 33069-62-4 taxol 

Relevant articles and documents

Improved protection and esterification of a precursor of the taxotere and taxol side chains

(4S,5R)-N-BOC-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylic acid 8 was prepared and efficiently esterified by conveniently protected baccatins 9a,b. Smooth deprotection in formic acid gave the N-deprotected intermediates of Taxotere and taxol. This protocol did not generate any epimerization at C-2′ and constitutes a pratical method to prepare Taxotere, taxol and analogs.