Product Name

  • Name

    Docetaxel intermediate

  • EINECS 1806241-263-5
  • CAS No. 114915-14-9
  • Article Data12
  • CAS DataBase
  • Density 1.503 g/cm3
  • Solubility
  • Melting Point
  • Formula C49H55Cl6NO18
  • Boiling Point 1064.656 °C at 760 mmHg
  • Molecular Weight 1158.69
  • Flash Point 597.682 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 114915-14-9 (Docetaxel intermediate)
  • Hazard Symbols
  • 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)-;
  • PSA 224.45000
  • LogP 3.65050

Synthetic route

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

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

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Stage #1: 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;
Stage #2: With water; sodium hydrogencarbonate In chloroform		88%
With methanol; toluene-4-sulfonic acid In chloroform at 20℃; for 3h;88%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

10-deacetyl-7,10-diTroc-baccatin III
114915-16-1

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

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃;87%
In water; ethyl acetate at 25 - 30℃; for 1h;
With sodium hydrogencarbonate In water at 55 - 65℃; for 2h;737.4 g
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

C44H45Cl6N3O16
174729-13-6

C44H45Cl6N3O16

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
With potassium hydrogencarbonate; triphenylphosphine In dichloromethane; water for 19h; Ambient temperature;63%
N-chloro-N-sodio-tert-butylcarbamate
73210-14-7

N-chloro-N-sodio-tert-butylcarbamate

A

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

B

C49H55Cl6NO18
114977-25-2

C49H55Cl6NO18

C

C49H55Cl6NO18
114915-26-3, 114977-26-3, 114977-27-4

C49H55Cl6NO18

D

C49H55Cl6NO18
114915-26-3, 114977-26-3, 114977-27-4

C49H55Cl6NO18

Conditions
ConditionsYield
With osmium(VIII) oxide; silver nitrate In acetonitrile; tert-butyl alcohol for 24h; Ambient temperature; var. solvents and temp.; Further byproducts given;A 25%
B 22%
C 21.5%
D 16.5%
...Expand
C57H61Cl6NO19
859498-31-0

C57H61Cl6NO19

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
With APTS In methanol at 20℃; for 16h;25%
With toluene-4-sulfonic acid In methanol at 20℃;
With hydrogenchloride In water; ethyl acetate at 20 - 24℃; Solvent; Temperature;
N-chloro-N-sodio-tert-butylcarbamate
73210-14-7

N-chloro-N-sodio-tert-butylcarbamate

C44H46Cl6O17
95603-47-7, 95672-97-2

C44H46Cl6O17

B

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

C

C49H55Cl6NO18
114977-25-2

C49H55Cl6NO18

D

C49H55Cl6NO18
114915-26-3, 114977-26-3, 114977-27-4

C49H55Cl6NO18

Conditions
ConditionsYield
With osmium(VIII) oxide; silver nitrate In toluene; tert-butyl alcohol at 4℃; for 24h; var. solvents and temp.; Further byproducts given;A 12%
B 20%
C 17%
D 18%
...Expand
methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate
124649-67-8

methyl (2S,3R)-3-phenyl-2,3-dihydroxypropanoate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: triethylamine / CH2Cl2 / 38 h / 0 °C
2: K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
3: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature
4: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C
5: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
6: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
(2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate
124605-43-2

(2S,3R)-(-)-methyl 3-hydroxy-3-phenyl-2-((p-tolylsulfonyl)oxy)propionate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
2: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature
3: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C
4: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate
99528-65-1

(2R,3R)-(+)-methyl 3-phenyloxiranecarboxylate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature
2: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C
3: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
4: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
methyl (2R,3S)-3-phenylglycidate
115794-67-7

methyl (2R,3S)-3-phenylglycidate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: NaOH / tetrahydrofuran; H2O / 0.33 h / Ambient temperature
2: 5.55 g / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 0.17 h / Ambient temperature
3: 76 percent / hexamethylphosphoramide, TiBr4 / CH2Cl2 / 18 h / 0 °C
4: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C
5: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
Methyl cinnamate
103-26-4

Methyl cinnamate

XCH2CO2Et

XCH2CO2Et

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 65 percent / AD-mix-β / 2-methyl-propan-2-ol; H2O / 18 h / Ambient temperature
2: triethylamine / CH2Cl2 / 38 h / 0 °C
3: K2CO3 / dimethylformamide; H2O / 24 h / Ambient temperature
4: 80 percent / LiOH*H2O / methanol; H2O / 1 h / Ambient temperature
5: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C
6: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
7: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
cis-2,3-epoxy-3-phenyl-1-propanoic acid
99528-64-0

cis-2,3-epoxy-3-phenyl-1-propanoic acid

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 1 h / 80 °C
2: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
3: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
C44H44Cl6O16
174847-58-6

C44H44Cl6O16

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 76 percent / hexamethylphosphoramide, TiBr4 / CH2Cl2 / 18 h / 0 °C
2: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C
3: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin
174729-12-5

13-O-((2R,3R)-3-phenylglycidoyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / sodium azide, methyl formate / methanol; H2O / 40 h / 50 °C / other reagent: tri-n-butyltinazide/ZnI2
2: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin
174729-14-7

13-O-((2S,3R)-3-bromo-2-hydroxy-3-phenylpropionyl)-7,10-O,O'-bis(2,2,2-trichloroethoxycarbonyl)-10-deacetylbaccatin

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C
2: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
(2R,3S)-3-phenyloxiranecarboxylic acid
79898-19-4

(2R,3S)-3-phenyloxiranecarboxylic acid

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 5.55 g / dicyclohexylcarbodiimide, 4-N,N-dimethylaminopyridine / toluene / 0.17 h / Ambient temperature
2: 76 percent / hexamethylphosphoramide, TiBr4 / CH2Cl2 / 18 h / 0 °C
3: 71 percent / sodium azide, 15-crown-5 / dimethylformamide / 18 h / 0 °C
4: 63 percent / KHCO3, PPh3 / CH2Cl2; H2O / 19 h / Ambient temperature
View Scheme
(2R,3S)-3-amino-2-hydroxy-3-phenylpropionic acid ethyl ester
143615-00-3

(2R,3S)-3-amino-2-hydroxy-3-phenylpropionic acid ethyl ester

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
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: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
5: 78 percent / HCOOH / 4 h / 20 °C
6: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester
144787-20-2

(2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
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: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
6: 78 percent / HCOOH / 4 h / 20 °C
7: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
benzaldehyde
100-52-7

benzaldehyde

aminoguanidine salt

aminoguanidine salt

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
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: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
9: 78 percent / HCOOH / 4 h / 20 °C
10: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III
95603-44-4

7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
2: 78 percent / HCOOH / 4 h / 20 °C
3: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: dmap; dicyclohexyl-carbodiimide / toluene / 50 °C
2: sodium carbonate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: dmap; dicyclohexyl-carbodiimide / toluene / 50 °C
2: sodium carbonate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C
3: triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid / tetrahydrofuran
View Scheme
ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate
126060-73-9

ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
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: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
7: 78 percent / HCOOH / 4 h / 20 °C
8: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
(2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine
143527-75-7

(2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 99 percent / pyridinium paratoluenesulfonate (PTSP) / toluene / 80 °C
2: 100 percent / LiOH, H2O / ethanol / 20 °C
3: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
4: 78 percent / HCOOH / 4 h / 20 °C
5: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid
143615-03-6, 143527-70-2

(4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
2: 78 percent / HCOOH / 4 h / 20 °C
3: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate
143527-74-6

ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 100 percent / LiOH, H2O / ethanol / 20 °C
2: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
3: 78 percent / HCOOH / 4 h / 20 °C
4: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
(4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one
144704-63-2

(4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
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: 98 percent / DCC, DMAP / toluene / 2 h / 80 °C
8: 78 percent / HCOOH / 4 h / 20 °C
9: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate
143527-76-8

4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 78 percent / HCOOH / 4 h / 20 °C
2: 87 percent / NaHCO3 / tetrahydrofuran / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: formic acid / 1 h / 25 - 35 °C
2: sodium hydrogencarbonate / water / 2 h / 55 - 65 °C
View Scheme
(3'S)-7,10-di-Troc-docetaxel

(3'S)-7,10-di-Troc-docetaxel

A

(2'R,3'S)-7,10-di-Troc-docetaxel
151636-78-1

(2'R,3'S)-7,10-di-Troc-docetaxel

B

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
With silica gel column (20 μM, 0.45*90 cm) In methanol; dichloromethane Purification / work up; Resolution of diastereomeric mixture;
(2'R,3'S)-7,10-di-Troc-docetaxel
151636-78-1

(2'R,3'S)-7,10-di-Troc-docetaxel

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Stage #1: (2'R,3'S)-7,10-di-Troc-docetaxel With triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid In tetrahydrofuran
Stage #2: With potassium hydroxide In tetrahydrofuran
Stage #1: (2'R,3'S)-7,10-di-Troc-docetaxel With triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid In tetrahydrofuran
Stage #2: With potassium hydroxide In tetrahydrofuran
(3'S)-2'-Ac-7,10-di-Troc-docetaxel

(3'S)-2'-Ac-7,10-di-Troc-docetaxel

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate; dihydrogen peroxide / water; tetrahydrofuran / 20 °C
2: triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid / tetrahydrofuran
View Scheme
(3'S)-2'-Ac-7,10-di-Troc-docetaxel

(3'S)-2'-Ac-7,10-di-Troc-docetaxel

A

(2'R,3'S)-7,10-di-Troc-docetaxel
151636-78-1

(2'R,3'S)-7,10-di-Troc-docetaxel

B

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Conditions
ConditionsYield
With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 20℃;
7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride
637330-41-7

N,N'-dimethyl-N-benzyl-[4-(2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)uronate-3-nitrobenzoyloxycarbonyl]ethylenediamine carbamoyl chloride

C93H126Cl6N4O30Si3

C93H126Cl6N4O30Si3

Conditions
ConditionsYield
With dmap In dichloromethane for 2h;93%
7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

Docetaxel
114915-20-7, 114977-28-5, 114977-29-6, 133577-32-9, 133577-33-0

Docetaxel

Conditions
ConditionsYield
With acetic acid; zinc In methanol at 60℃; for 2h;90%
With acetic acid; zinc In methanol at 60℃; for 1h;90%
Product distribution / selectivity;90%
7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

10-deacetyl-7,10-diTroc-baccatin III
114915-16-1

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

Conditions
ConditionsYield
With trimethylsilyl iodide In acetonitrile at 0℃; for 0.5h;75%
With formic acid at 18℃; for 1.5h; Temperature;25.3 g
glutaric anhydride,
108-55-4

glutaric anhydride,

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel
114915-14-9

7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel

C54H61Cl6NO21

C54H61Cl6NO21

Conditions
ConditionsYield
With pyridine at -20 - 25℃;60%

Docetaxel intermediate Specification

The CAS registry number of Docetaxel intermediate is 114915-14-9. The IUPAC name is (2α,5β,7β,10β,13α)-4-(acetyloxy)-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-epoxy tax-11-en-2-yl benzoate. In addition, the molecular formula is C49H55Cl6NO18 and the molecular weight is 1158.6749.

Physical properties about this chemical are: (1)ACD/LogP: 7.71; (2)# of Rule of 5 Violations: 3; (3)ACD/LogD (pH 5.5): 12; (4)ACD/LogD (pH 7.4): 12; (5)ACD/BCF (pH 5.5): 1000000; (6)ACD/BCF (pH 7.4): 1000000; (7)ACD/KOC (pH 5.5): 10000000; (8)ACD/KOC (pH 7.4): 10000000; (9)#H bond acceptors: 19; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 23; (12)Polar Surface Area: 255.05 Å2; (13)Index of Refraction: 1.607; (14)Molar Refractivity: 266.178 cm3; (15)Molar Volume: 771.11 cm3; (16)Polarizability: 105.521 ×10-24cm3; (17)Surface Tension: 65.667 dyne/cm; (18)Density: 1.503 g/cm3; (19)Flash Point: 597.682 °C; (20)Enthalpy of Vaporization: 163.395 kJ/mol; (21)Boiling Point: 1064.656 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC(C)(C)C)N[C@@H](c1ccccc1)[C@@H](O)C(=O)O[C@@H]4C(=C3/[C@@H](OC(=O)OCC(Cl)(Cl)Cl)C(=O)[C@]6([C@H]([C@H](OC(=O)c2ccccc2)[C@@](O)(C3(C)C)C4)[C@@]5(OC(=O)C)[C@H](OC5)C[C@@H]6OC(=O)OCC(Cl)(Cl)Cl)C)/C
(2)InChI: InChI=1/C49H55Cl6NO18/c1-24-28(69-39(61)33(58)32(26-15-11-9-12-16-26)56-40(62)74-43(3,4)5)20-47(65)37(72-38(60)27-17-13-10-14-18-27)35-45(8,36(59)34(31(24)44(47,6)7)71-42(64)68-23-49(53,54)55)29(70-41(63)67-22-48(50,51)52)19-30-46(35,21-66-30)73-25(2)57/h9-18,28-30,32-35,37,58,65H,19-23H2,1-8H3,(H,56,62)/t28-,29-,30+,32-,33+,34+,35-,37-,45+,46-,47+/m0/s1
(3)InChIKey: QTCVMFMWHTVJTQ-LNJGEEBYBK

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