Product Name

  • Name

    IXABEPILONE

  • EINECS 630-424-7
  • CAS No. 219989-84-1
  • Article Data6
  • CAS DataBase
  • Density 1.122 g/cm3
  • Solubility
  • Melting Point
  • Formula C27H42N2O5S
  • Boiling Point 697.815 °C at 760 mmHg
  • Molecular Weight 506.707
  • Flash Point 375.825 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 219989-84-1 (IXABEPILONE)
  • Hazard Symbols
  • Synonyms AzaepothiloneB;BMS 247550;BMS 247550-1;Ixempra;
  • PSA 140.29000
  • LogP 4.37930

Synthetic route

[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
219989-87-4

[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

ixabepilone
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

(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

ixabepilone
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%
(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
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

ixabepilone
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
C29H47N3O7S
1417803-30-5

C29H47N3O7S

ixabepilone
219989-84-1

ixabepilone

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

ixabepilone
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
epothilone B
152044-54-7

epothilone B

ixabepilone
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
(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
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

ixabepilone
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
(5R)-5-hydroxy-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
277749-45-8

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

ixabepilone
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
(5S)-5-azido-2-iodo-6-methyl-7-(2-methylthiazol-4-yl)-2,6-heptadiene
277749-36-7

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

ixabepilone
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

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

ixabepilone
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
Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-azacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester
277749-43-6

Carbonic acid (Z)-(4S,7R,8S,9S,16S)-4-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-2,6-dioxo-azacyclohexadec-13-en-8-yl ester 2,2,2-trichloro-ethyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
2: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(3S,6R,7S,8S,15S)-15-Amino-3-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid
350042-12-5

(12Z,16E)-(3S,6R,7S,8S,15S)-15-Amino-3-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
2: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
3: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Amino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-19-2

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Amino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
2: 82 percent / p-TsOH / acetone / 22 h / 20 °C
3: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
4: TFA / CH2Cl2 / 2 h / 20 °C
5: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
6: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
7: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Azido-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-09-0

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-Azido-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: tetrahydrofuran / 19 h / 40 °C
2: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
3: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
4: 82 percent / p-TsOH / acetone / 22 h / 20 °C
5: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
6: TFA / CH2Cl2 / 2 h / 20 °C
7: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
8: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
9: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester
277749-41-4

(12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-3,5-dioxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
2: TFA / CH2Cl2 / 2 h / 20 °C
3: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
4: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
5: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(2Z,12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester
350042-11-4

(2Z,12Z,16E)-(6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-methoxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-2,12,16-trienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 82 percent / p-TsOH / acetone / 22 h / 20 °C
2: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
3: TFA / CH2Cl2 / 2 h / 20 °C
4: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
5: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
6: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(12Z,16E)-(3S,6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester
277749-42-5

(12Z,16E)-(3S,6R,7S,8S,15S)-15-tert-Butoxycarbonylamino-3-hydroxy-4,4,6,8,12,16-hexamethyl-17-(2-methyl-thiazol-4-yl)-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-heptadeca-12,16-dienoic acid tert-butyl ester

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: TFA / CH2Cl2 / 2 h / 20 °C
2: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
3: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
4: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(Z)-(6R,7S,8S)-11-(9-Bora-bicyclo[3.3.1]non-9-yl)-3-methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undec-2-enoic acid tert-butyl ester

(Z)-(6R,7S,8S)-11-(9-Bora-bicyclo[3.3.1]non-9-yl)-3-methoxy-4,4,6,8-tetramethyl-5-oxo-7-(2,2,2-trichloro-ethoxycarbonyloxy)-undec-2-enoic acid tert-butyl ester

ixabepilone
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
C35H51Cl3N2O7SP(C6H5)3

C35H51Cl3N2O7SP(C6H5)3

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 3.9 g / H2O / tetrahydrofuran / 4 h / 65 °C
2: 70 percent / Et3N / acetonitrile / 16 h / 20 °C
3: 82 percent / p-TsOH / acetone / 22 h / 20 °C
4: 78 percent / Et2NH2[{((R)-BINAP)RuCl}2Cl2]; HCl / methanol / 18 h / 25 °C / 62059.4 Torr
5: TFA / CH2Cl2 / 2 h / 20 °C
6: 79 percent / HOAt; DIPEA; HATU / CH2Cl2; dimethylformamide / 16 h / 25 °C
7: 88 percent / Zn; AcOH / tetrahydrofuran / 2 h / 25 °C
8: 69 percent / DMDO / CH2Cl2 / 1 h / -78 - -50 °C
View Scheme
(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde
184246-38-6

(E)-2-methyl-3-(2-methylthiazol-4-yl)acrylaldehyde

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
2.2: -50 - 20 °C
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
6.2: 0.5 h / -60 - -50 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
2.2: -50 - 20 °C
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
6.2: 0.42 h / -20 °C
6.3: 1 h / -20 - 10 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 11 steps
1.1: titanium(IV) isopropylate / tetrahydrofuran / 20 °C / Inert atmosphere
2.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
2.2: 6 h / -78 °C / Inert atmosphere
3.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
4.1: triethylamine / tetrahydrofuran / 20 °C
5.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
5.2: 0.5 h / 30 °C
5.3: 1 h / 30 °C
6.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
6.2: 0.5 h / -60 - -50 °C
7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
7.2: 0.5 h
7.3: 50 °C
8.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
11.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C15H24N2OS2

C15H24N2OS2

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
3.2: 0.5 h / 30 °C
3.3: 1 h / 30 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
3.2: 0.5 h / 30 °C
3.3: 1 h / 30 °C
4.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
4.2: 0.42 h / -20 °C
4.3: 1 h / -20 - 10 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
2.1: triethylamine / tetrahydrofuran / 20 °C
3.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(S)-4-[3-[N-[(tert-butyloxy)carbonyl]amino]-2-methyl-1(E),5-hexadienyl]-2-methylthiazole
219990-13-3

(S)-4-[3-[N-[(tert-butyloxy)carbonyl]amino]-2-methyl-1(E),5-hexadienyl]-2-methylthiazole

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
2.2: 0.42 h / -20 °C
2.3: 1 h / -20 - 10 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
1.2: 0.5 h / 30 °C
1.3: 1 h / 30 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C16H26N2O4S

C16H26N2O4S

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
2.2: 0.42 h / -20 °C
2.3: 1 h / -20 - 10 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
5.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 8 steps
1.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
2.2: 0.5 h / -60 - -50 °C
3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
3.2: 0.5 h
3.3: 50 °C
4.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
5.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
6.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
7.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
8.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C15H22N2O3S

C15H22N2O3S

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
1.2: 0.5 h / -60 - -50 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 6 steps
1.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
1.2: 0.42 h / -20 °C
1.3: 1 h / -20 - 10 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
4.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
6.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 7 steps
1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
1.2: 0.5 h / -60 - -50 °C
2.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
2.2: 0.5 h
2.3: 50 °C
3.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
4.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
5.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
6.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
7.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
C12H18N2OS2

C12H18N2OS2

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
1.2: -50 - 20 °C
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: dichloromethane / 1.5 h / -50 °C / Inert atmosphere
1.2: -50 - 20 °C
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
5.2: 0.42 h / -20 °C
5.3: 1 h / -20 - 10 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: zinc / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere
1.2: 6 h / -78 °C / Inert atmosphere
2.1: water; hydrogenchloride / 1,4-dioxane / 5 - 20 °C
3.1: triethylamine / tetrahydrofuran / 20 °C
4.1: 4-methylmorpholine N-oxide; potassium osmate monohydrate / water; acetone / 3 h / 30 °C
4.2: 0.5 h / 30 °C
4.3: 1 h / 30 °C
5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
5.2: 0.5 h / -60 - -50 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
6.2: 0.5 h
6.3: 50 °C
7.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
8.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
9.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 30 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(S)-4-(3-amino-2-methyl-1(E),5-hexadienyl)-2-methylthiazole
219990-14-4

(S)-4-(3-amino-2-methyl-1(E),5-hexadienyl)-2-methylthiazole

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C
2.2: 20 °C
3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 18 h / 0 - 20 °C
4.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
5.1: n-butyllithium; iodine / tetrahydrofuran / 0.08 h / -80 - 1 °C / Inert atmosphere
5.2: 0.08 h / -20 °C
5.3: 1 h / -20 - 10 °C
6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 1 h / 20 °C
6.2: 0.5 h
6.3: 0.5 h / 20 °C
7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
7.1: water; dihydrogen peroxide; lithium hydroxide / tetrahydrofuran; methanol / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
Multi-step reaction with 10 steps
1.1: triethylamine / tetrahydrofuran / 20 °C
2.1: 4-methylmorpholine N-oxide; hydroquinidein 1,4-phthalazinediyl diether; potassium osmate(VI) dihydrate / tetrahydrofuran; water / 1 h / 0 - 25 °C
3.1: sodium periodate / tetrahydrofuran; water / 0.67 h / 0 °C
4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -25 - -20 °C / Inert atmosphere
4.2: 0.5 h / -60 - -50 °C
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 3 h / 20 °C
5.2: 0.5 h
5.3: 50 °C
6.1: water; dihydrogen peroxide; sodium hydroxide / 2-methyltetrahydrofuran; methanol / 0 - 25 °C
7.1: 2,6-dimethylpyridine; trimethylsilyl trifluoromethanesulfonate / dichloromethane / 1 h / 0 - 20 °C
8.1: HATU; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 5.5 h / 30 °C
9.1: trifluoroacetic acid / dichloromethane / 6 h / 0 °C
10.1: 3,3-dimethyldioxirane / dichloromethane; acetone / 1.5 h / -78 - -50 °C / Inert atmosphere
View Scheme
(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one
188899-12-9

(-)-(3S)-3,5-bis(tert-butyldimethylsilyloxy)-pentan-2-one

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 18 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
7.2: 1 h / -78 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
13.2: 3 h / 0 - 30 °C / Inert atmosphere
14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
15.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
16.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
17.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
18.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 18 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
7.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
7.2: 1 h / -78 °C
8.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
10.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
11.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
13.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
13.2: 3 h / 0 - 30 °C / Inert atmosphere
14.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
15.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
17.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
18.1: 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
Multi-step reaction with 19 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
1.2: 14 h / -75 - 30 °C
2.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
4.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
4.2: 0.75 h / -75 - -35 °C / Inert atmosphere
5.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
5.2: 2 h / 25 - 30 °C / Inert atmosphere
6.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
7.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
8.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
8.2: 1 h / -78 °C
9.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
10.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
11.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
12.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
13.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
14.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
14.2: 3 h / 0 - 30 °C / Inert atmosphere
15.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
16.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
17.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
18.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
19.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-3,5-dihydroxypentanenitrile

(R)-3,5-dihydroxypentanenitrile

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 24 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 24 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
24.1: 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
Multi-step reaction with 25 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
2.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
3.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
4.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
5.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
6.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
6.2: 2 h / 70 - 75 °C
7.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
7.2: 14 h / -75 - 30 °C
8.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
9.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
10.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
10.2: 0.75 h / -75 - -35 °C / Inert atmosphere
11.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
11.2: 2 h / 25 - 30 °C / Inert atmosphere
12.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
13.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-ethyl 4-cyano-3-hydroxybutyrate
141942-85-0

(R)-ethyl 4-cyano-3-hydroxybutyrate

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 25 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
23.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
24.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
25.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 25 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
14.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
14.2: 1 h / -78 °C
15.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
16.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
17.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
18.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
19.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
20.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
20.2: 3 h / 0 - 30 °C / Inert atmosphere
21.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
22.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
24.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
25.1: 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
Multi-step reaction with 26 steps
1.1: sodium tetrahydroborate; methanol / 8.25 h / 0 - 30 °C
2.1: 1H-imidazole / N,N-dimethyl-formamide / 7 h / 25 - 70 °C
3.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
4.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
5.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
6.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
7.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
7.2: 2 h / 70 - 75 °C
8.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
8.2: 14 h / -75 - 30 °C
9.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
10.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
11.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
11.2: 0.75 h / -75 - -35 °C / Inert atmosphere
12.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
12.2: 2 h / 25 - 30 °C / Inert atmosphere
13.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
14.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
15.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
15.2: 1 h / -78 °C
16.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
17.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
18.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
19.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
20.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
21.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
21.2: 3 h / 0 - 30 °C / Inert atmosphere
22.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
23.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
24.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
25.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
26.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
(R)-3,5-bis(tert-butyldimethylsilyloxy)pentanenitrile

(R)-3,5-bis(tert-butyldimethylsilyloxy)pentanenitrile

ixabepilone
219989-84-1

ixabepilone

Conditions
ConditionsYield
Multi-step reaction with 23 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
12.2: 1 h / -78 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
18.2: 3 h / 0 - 30 °C / Inert atmosphere
19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
20.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
21.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
22.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
23.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
Multi-step reaction with 23 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 6 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: diisobutylaluminium hydride / toluene / 2 h / -78 °C / Inert atmosphere
12.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
12.2: 1 h / -78 °C
13.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
14.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
15.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
16.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
17.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
18.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
18.2: 3 h / 0 - 30 °C / Inert atmosphere
19.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
20.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 30 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
23.1: 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
Multi-step reaction with 24 steps
1.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -75 - -70 °C / Inert atmosphere
2.1: sodium tetrahydroborate; methanol / 2 h / 0 - 30 °C
3.1: 1H-imidazole; iodine; triphenylphosphine / dichloromethane / 1 h / 0 - 30 °C
4.1: potassium tert-butylate / tetrahydrofuran / 1.5 h / 0 - 5 °C / Inert atmosphere
5.1: palladium dichloride; copper(l) chloride; oxygen / water; N,N-dimethyl-formamide / 1.25 h / 45 - 50 °C / 1125.11 Torr / Autoclave
5.2: 2 h / 70 - 75 °C
6.1: n-butyllithium / tetrahydrofuran / 1 h / -75 - -70 °C / Inert atmosphere
6.2: 14 h / -75 - 30 °C
7.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 5.5 h / -10 - 5 °C
8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1.5 h / 0 - 30 °C / Inert atmosphere
9.1: n-butyllithium / tetrahydrofuran / 0.5 h / -5 - 35 °C / Inert atmosphere
9.2: 0.75 h / -75 - -35 °C / Inert atmosphere
10.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 25 - 30 °C / Inert atmosphere
10.2: 2 h / 25 - 30 °C / Inert atmosphere
11.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
12.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
13.1: n-butyllithium; diisopropylamine / tetrahydrofuran / 1.08 h / -78 - -35 °C / Inert atmosphere
13.2: 1 h / -78 °C
14.1: 2,6-dimethylpyridine / dichloromethane / 4.5 h / 0 - 30 °C / Inert atmosphere
15.1: (1S)-10-camphorsulfonic acid / dichloromethane; methanol / 3.5 h / -10 - 0 °C
16.1: Dess-Martin periodane / dichloromethane; pyridine / 2 h / 0 - 30 °C / Inert atmosphere
17.1: sodium chlorite; sodium dihydrogenphosphate dihydrate / water; tert-butyl alcohol / 2 h / 0 - 30 °C
18.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 12 h / 0 - 30 °C / Inert atmosphere
19.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1 h / 0 - 5 °C / Inert atmosphere
19.2: 3 h / 0 - 30 °C / Inert atmosphere
20.1: trifluoroacetic acid / dichloromethane / 0.75 h / 0 - 5 °C / Inert atmosphere
21.1: tetrakis(triphenylphosphine) palladium(0); sodium azide / water; tetrahydrofuran / 1 h / 25 - 50 °C / Inert atmosphere
22.1: trimethylphosphane / water; tetrahydrofuran / 3 h / 25 - 30 °C / Inert atmosphere
23.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / acetonitrile; N,N-dimethyl-formamide / 12 h / 0 - 30 °C / Inert atmosphere
24.1: 3-chloro-benzenecarboperoxoic acid / chloroform / 4 h / -20 - -15 °C / Inert atmosphere
View Scheme
triethylsilyl chloride
994-30-9

triethylsilyl chloride

ixabepilone
219989-84-1

ixabepilone

(1S,3S,7S,10R,11S,12S,16R)-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis[(triethylsilyl)-oxy]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione

(1S,3S,7S,10R,11S,12S,16R)-8,8,10,12,16-pentamethyl-3-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-7,11-bis[(triethylsilyl)-oxy]-17-oxa-4-azabicyclo[14.1.0]heptadecane-5,9-dione

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; for 18h;92%
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 25℃; for 2.16667h; Inert atmosphere;89%
ixabepilone
219989-84-1

ixabepilone

A

[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
219989-87-4

[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

B

[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(E)-cyclohexadecene-2,6-dione

[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(E)-cyclohexadecene-2,6-dione

Conditions
ConditionsYield
With n-butyllithium; tungsten(VI) chloride In tetrahydrofuran; hexane at 25℃; for 0.5h;A 47%
B 9.1%
phosgene
75-44-5

phosgene

2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride

2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride

ixabepilone
219989-84-1

ixabepilone

C35H50N4O6S3

C35H50N4O6S3

Conditions
ConditionsYield
Stage #1: phosgene; ixabepilone With triethylamine In dichloromethane; toluene for 0.5h;
Stage #2: 2-(pyridin-2-yldisulfanyl)ethan-1-amine hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane; toluene for 1h;		49%
...Expand
octadecanedioic acid mono-triisopropylsilyl ester

octadecanedioic acid mono-triisopropylsilyl ester

ixabepilone
219989-84-1

ixabepilone

C54H94N2O8SSi

C54H94N2O8SSi

Conditions
ConditionsYield
Stage #1: ixabepilone With dmap; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane at 0℃; for 0.166667h;
Stage #2: octadecanedioic acid mono-triisopropylsilyl ester In dichloromethane at 0 - 20℃;
6-(2,2,2-trichloroethoxycarbonylamino)hexanoic acid
130332-90-0

6-(2,2,2-trichloroethoxycarbonylamino)hexanoic acid

ixabepilone
219989-84-1

ixabepilone

A

C36H54Cl3N3O8S

C36H54Cl3N3O8S

B

C36H54Cl3N3O8S

C36H54Cl3N3O8S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 12h; Inert atmosphere;
...Expand
tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

ixabepilone
219989-84-1

ixabepilone

A

7-tert-butyl dimethylsilyl ixabepilone

7-tert-butyl dimethylsilyl ixabepilone

B

C33H56N2O5SSi

C33H56N2O5SSi

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;
...Expand

Ixabepilone 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 

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