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114915-14-9

Basic Information
CAS No.: 114915-14-9
Name: Docetaxel intermediate
Article Data: 12
Molecular Structure:
Molecular Structure of 114915-14-9 (Docetaxel intermediate)
Formula: C49H55Cl6NO18
Molecular Weight: 1158.69
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)-;
EINECS: 1806241-263-5
Density: 1.503 g/cm3
Boiling Point: 1064.656 °C at 760 mmHg
Flash Point: 597.682 °C
PSA: 224.45000
LogP: 3.65050
Synthetic route
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

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%
24424-99-5

di-tert-butyl dicarbonate

114915-16-1

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

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
24424-99-5

di-tert-butyl dicarbonate

174729-13-6

C44H45Cl6N3O16

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%
73210-14-7

N-chloro-N-sodio-tert-butylcarbamate

A

114915-14-9

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

B

114977-25-2

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%
859498-31-0

C57H61Cl6NO19

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;
73210-14-7

N-chloro-N-sodio-tert-butylcarbamate

B

114915-14-9

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

C

114977-25-2

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%
124649-67-8

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

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
124605-43-2

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

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
99528-65-1

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

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
115794-67-7

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

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
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  • intermediate for Docetaxel

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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