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219989-84-1

Basic Information
CAS No.: 219989-84-1
Name: IXABEPILONE
Article Data: 6
Molecular Structure:
Molecular Structure of 219989-84-1 (IXABEPILONE)
Formula: C27H42N2O5S
Molecular Weight: 506.707
Synonyms: AzaepothiloneB;BMS 247550;BMS 247550-1;Ixempra;
EINECS: 630-424-7
Density: 1.122 g/cm3
Boiling Point: 697.815 °C at 760 mmHg
Flash Point: 375.825 °C
PSA: 140.29000
LogP: 4.37930
Synthetic route
219989-87-4

[4S-[4R*,7S*,8R*,9R*,15R*(E)]]-4,8-dihydroxy-5,5,7,9,13-pentamethyl-16-[1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-1-aza-13(Z)-cyclohexadecene-2,6-dione

219989-84-1

ixabepilone

Conditions
ConditionsYield
With DMDO In dichloromethane at -78 - -50℃; for 1h;69%
With 3,3-dimethyldioxirane In dichloromethane; acetone at -78 - -50℃; for 1.5h; Inert atmosphere;42.8%
With 3-chloro-benzenecarboperoxoic acid In chloroform at -20 - -15℃; for 4h; Inert atmosphere;0.31 g

(3S,6R,7S,8S,12R,13S,15S)-15-amino-12,13-epoxy-4,4,6,8,12,16-hexamethyl-3,7-dihydroxy-17-(2-methyl-4-thiazolyl)-5-oxo-16-heptadecenoic acid

219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0 - 4℃; for 24h; Inert atmosphere;40%
219990-25-7

(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-amino-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid

219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl-phosphinic acid; sodium hydrogencarbonate In N,N-dimethyl-formamide at 4℃; for 24h;43%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide; acetonitrile at 0 - 30℃; for 12h; Inert atmosphere;3.2 g
1417803-30-5

C29H47N3O7S

219989-84-1

ixabepilone

Conditions
ConditionsYield
With diphenyl phosphoryl azide; sodium hydrogencarbonate In N,N-dimethyl-formamide at 0℃; for 24h; Inert atmosphere;
219990-23-5

(3S,6R,7S,8S)-11-((2R,3S)-3-((S,E)-2-azido-3-methyl-4-(2-methylthiazol-4-yl)but-3-enyl)-2-methyloxiran-2-yl)-3,7-dihydroxy-4,4,6,8-tetramethyl-5-oxoundecanoic acid

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 71 percent / PMe3; H2O / tetrahydrofuran; toluene / 2 h / 25 °C
2: 43 percent / DPPA; NaHCO3 / dimethylformamide / 24 h / 4 °C
View Scheme
Multi-step reaction with 2 steps
1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
2: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
152044-54-7

epothilone B

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0) / tetrahydrofuran / 0.5 h / 25 °C / Inert atmosphere
1.2: 1 h / 45 °C
2.1: triphenylphosphine / tetrahydrofuran / 14 h / 45 °C / Inert atmosphere
2.2: 4 h / 45 °C
3.1: sodium hydrogencarbonate; diphenyl phosphoryl azide / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
2: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
View Scheme
224580-49-8

(Z)-(6R,7S,8S)-3-Methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undeca-2,10-dienoic acid tert-butyl ester

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: tetrahydrofuran / 1 h / 25 °C
2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
3: tetrahydrofuran / 19 h / 40 °C
4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
6: 82 percent / p-TsOH / acetone / 22 h / 20 °C
7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
8: TFA / CH2Cl2 / 2 h / 20 °C
9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
277749-45-8

(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C
2: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
3: tetrahydrofuran / 19 h / 40 °C
4: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
5: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
6: 82 percent / p-TsOH / acetone / 22 h / 20 °C
7: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
8: TFA / CH2Cl2 / 2 h / 20 °C
9: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
10: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
11: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
277749-36-7

(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
2: tetrahydrofuran / 19 h / 40 °C
3: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
4: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
5: 82 percent / p-TsOH / acetone / 22 h / 20 °C
6: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
7: TFA / CH2Cl2 / 2 h / 20 °C
8: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
9: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
10: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme

4-((1E,5Z)-(R)-6-Iodo-2-methyl-3-triethylsilanyloxy-hepta-1,5-dienyl)-2-methyl-thiazole

219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 12 steps
1: 99 percent / aq. AcOH / tetrahydrofuran / 8 h / 20 °C
2: 85 percent / diphenylphosphoryl azide; DBU / toluene / 2 h / 2 - 25 °C
3: 70 percent / Pd(dppf)Cl2*CH2Cl2; AsPh3; Cs2CO3 / dimethylformamide; H2O; tetrahydrofuran / 2 h
4: tetrahydrofuran / 19 h / 40 °C
5: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
6: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
7: 82 percent / p-TsOH / acetone / 22 h / 20 °C
8: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
9: TFA / CH2Cl2 / 2 h / 20 °C
10: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
11: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
12: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
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Specification

The Ixabepilone, with the CAS registry number 219989-84-1, is also known as Azaepothilone B. This chemical's molecular formula is C27H42N2O5S and molecular weight is 506.70. What's more, its systematic name is (1R,5S,6S,7R,10S,14S,16S)-6,10-dihydroxy-1,5,7,9,9-pentamethyl-14-[(E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-17-oxa-13-azabicyclo[14.1.0]heptadecane-8,12-dione. Its classification codes are: (1)Antimitotic; (2)Antineoplastic; (3)Antineoplastic Agents. Ixabepilone, in combination with capecitabine, has demonstrated effectiveness in the treatment of metastatic or locally advanced breast cancer in patients after failure of an anthracycline and a taxane. It has been investigated for use in treatment of non-Hodgkin's lymphoma. 

Physical properties of Ixabepilone are: (1)ACD/LogP: 1.772; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.77; (4)ACD/LogD (pH 7.4): 1.77; (5)ACD/BCF (pH 5.5): 13.07; (6)ACD/BCF (pH 7.4): 13.09; (7)ACD/KOC (pH 5.5): 218.97; (8)ACD/KOC (pH 7.4): 219.36; (9)#H bond acceptors: 7; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 140.29 Å2; (13)Index of Refraction: 1.532; (14)Molar Refractivity: 140.117 cm3; (15)Molar Volume: 451.556 cm3; (16)Polarizability: 55.547×10-24cm3; (17)Surface Tension: 40.93 dyne/cm; (18)Density: 1.122 g/cm3; (19)Flash Point: 375.825 °C; (20)Enthalpy of Vaporization: 107.302 kJ/mol; (21)Boiling Point: 697.815 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: Cc3nc(/C=C(\C)[C@@H]1C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)N1)cs3
(2)Std. InChI: InChI=1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
(3)Std. InChIKey: FABUFPQFXZVHFB-PVYNADRNSA-N