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129453-61-8

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Basic Information
CAS No.: 129453-61-8
Name: Fulvestrant
Molecular Structure:
Molecular Structure of 129453-61-8 (Fulvestrant)
Formula: C32H47F5O3S
Molecular Weight: 606.77
Synonyms: Faslodex;Estra-1,3,5(10)-triene-3,17-diol,7-[9-[(4,4,5,5,5-pentafluoropentyl)sulfinyl]nonyl]-, (7a,17b)-;ICI 182780;ZD 182780;ZD 9238;ZM 182780;
EINECS: 642-998-6
Density: 1.201 g/cm3
Melting Point: 104-106°C
Boiling Point: 674.8 °C at 760 mmHg
Flash Point: 361.9 °C
Solubility:
Appearance: white powder
Hazard Symbols:
Risk Codes:
Safety:
Transport Information:
PSA: 76.74000
LogP: 9.54830
Related products
Synthetic route
153004-31-0

(+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol

129453-61-8

fulvestrant

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In water; ethyl acetate at 40℃; for 4h; Inert atmosphere; Schlenk technique;95%
Stage #1: (+)-(7α)-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5(10)-triene-3,17β-diol With β‐cyclodextrin In water; acetone at 20 - 60℃; for 0.5h;
Stage #2: With N-Bromosuccinimide In water; acetone at 40℃; for 10h; Temperature;		87%
With dihydrogen peroxide; acetic acid In water; ethyl acetate for 6 - 8h;85%

7β-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5-trien-3,17β-diol

129453-61-8

fulvestrant

Conditions
ConditionsYield
With dihydrogen peroxide; acetic acid In ethyl acetate82%
1221256-46-7

(7R,13S)-3-methoxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-17-ol

129453-61-8

fulvestrant

Conditions
ConditionsYield
With aluminum (III) chloride; thiourea In dichloromethane at 20 - 55℃; Product distribution / selectivity;32%
261506-24-5

ICI 182,780-17β-acetate

129453-61-8

fulvestrant

Conditions
ConditionsYield
With methanol; potassium hydroxide at 20℃; for 3h; Product distribution / selectivity;

7-[9-(4,4,5,5,5-pentafluoropentylsulfanyl)nonyl]estra-1,3,5-trien-3,17β-diol

129453-61-8

fulvestrant

Conditions
ConditionsYield
With dihydrogen peroxide In water; acetic acid; ethyl acetate at 23℃; for 8h; Large scale reaction;88.4 kg
148043-73-6

4,4,5,5,5-pentafluorpentan-1-ol

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
2: isopropyl alcohol / 10 h / Reflux; Inert atmosphere
3: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
4: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
5: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 17 h / 0 - 20 °C
2.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
3.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
3.2: Reflux
4.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme
Multi-step reaction with 4 steps
1: triethylamine; dmap / dichloromethane / 1 h / -10 °C
2: ethanol / 6 h / 65 °C
3: N,N-dimethyl-formamide / 20 °C
4: acetic acid; dihydrogen peroxide / ethyl acetate
View Scheme
252947-01-6

1-methanesulfonyloxy-4,4,5,5,5-pentafluoropentane

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: isopropyl alcohol / 10 h / Reflux; Inert atmosphere
2: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
3: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: ethanol / Reflux
2: sodium hydroxide / water; methanol / 24 h / Inert atmosphere; Reflux
3: sodium periodate / water; methanol / 24 h / 20 °C / Cooling with ice
View Scheme
434-22-0

19-nortestosterone

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: potassium acetate; oxygen / N,N-dimethyl-formamide / 12 h / 20 - 120 °C / 6000.6 Torr / Autoclave
2.1: trichlorophosphate / dichloromethane / 4 h / 35 °C
3.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C
3.2: 3 h / 10 - 100 °C
4.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
5.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
6.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / 1 h / Reflux
2.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
2.2: 2 h / 0 °C / Reflux; Inert atmosphere
3.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
3.2: 0.5 h / -20 - 20 °C
4.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
5.1: water; sodium hydroxide / methanol / 5 h / 20 °C
6.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
7.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 7 steps
1.1: toluene-4-sulfonic acid / 1 h / Reflux
2.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
2.2: 2 h / 0 °C / Reflux; Inert atmosphere
3.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
3.2: 0.5 h / -20 - 20 °C
4.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
5.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
6.1: water; sodium hydroxide / methanol / 5 h / 20 °C
7.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
571-92-6

6-ketoestradiol

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: trichlorophosphate / dichloromethane / 4 h / 35 °C
2.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C
2.2: 3 h / 10 - 100 °C
3.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
4.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
5.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

(8R,9S,13S,14S,17S)-3,17-Bis-(1-methoxy-1-methyl-ethoxy)-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-cyclopenta[a]phenanthren-6-one

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: potassium tert-butylate / toluene / 1 h / 20 - 50 °C
1.2: 3 h / 10 - 100 °C
2.1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
3.1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
4.1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

C35H55BrO5

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylsilane; boron trifluoride diethyl etherate / dichloromethane / 4 h / 0 - 25 °C
2: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
3: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

C35H57BrO4

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
2: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

C40H63F5O4S

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
2: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme

carbamimidothioic acid 4,4,5,5,5-pentafluoropentyl mesylate ester

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / acetonitrile; triethylamine; water / 3 h / 70 °C
2: sodium hydrogensulfate monohydrate / dichloromethane; water / 3 h / Reflux
3: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 0 - 5 °C
View Scheme
875573-66-3

(+)-(7α)-[9-bromononyl]estra-1,3,5(10)-triene-3-ol-17β-yl acetate

148757-88-4

4,4,5,5,5-pentafluoro-1-pentanethiol

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
2: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
160598-75-4

1-(acetylsulfanyl)-4,4,5,5,5-pentafluoropentane

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / methanol / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique
2: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
3: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
89359-54-6

9-bromo-1-nonene

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Schwartz's reagent / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique
1.3: 20 °C / Inert atmosphere; Schlenk technique
2.1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
4.1: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
2590-41-2

6-dehydro-19-nortestosterone acetate

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Schwartz's reagent / dichloromethane / 0.33 h / 20 °C / Inert atmosphere; Schlenk technique
1.2: 0.17 h / 20 °C / Inert atmosphere; Schlenk technique
1.3: 20 °C / Inert atmosphere; Schlenk technique
2.1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique
3.1: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
4.1: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 5 steps
1.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
1.2: 0.5 h / -20 - 20 °C
2.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
3.1: water; sodium hydroxide / methanol / 5 h / 20 °C
4.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
5.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
1.2: 0.5 h / -20 - 20 °C
2.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
3.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
4.1: water; sodium hydroxide / methanol / 5 h / 20 °C
5.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
875573-63-0

(+)-3-oxo-(7α)-[9-bromononyl]estr-4-en-17β-ylacetate

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: lithium bromide; copper(ll) bromide / acetonitrile / 2 h / 20 °C / Inert atmosphere; Schlenk technique
2: methanol / 2 h / 40 °C / Inert atmosphere; Schlenk technique
3: dihydrogen peroxide; acetic acid / water; ethyl acetate / 4 h / 40 °C / Inert atmosphere; Schlenk technique
View Scheme
Multi-step reaction with 4 steps
1: copper(ll) bromide; lithium bromide / acetonitrile / 3 h / 20 °C / Large scale
2: hydrogen bromide / methanol / 3 h / Reflux; Large scale
3: sodium hydroxide / N,N-dimethyl-formamide; water / 1.5 h / 0 - 15 °C / Large scale
4: acetic acid; dihydrogen peroxide / ethyl acetate / 8 h / 20 - 30 °C / Large scale
View Scheme

C37H55BrO5

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
2.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
2.2: Reflux
3.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme
862700-61-6

thiobenzoic acid S-(4,4,5,5,5-pentafluoro-pentyl)ester

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
2.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
2.2: Reflux
3.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme
122566-22-7

(8R,9S,13S,14S,17S)-13-Methyl-3,17-bis-(tetrahydro-pyran-2-yloxy)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-6-ol

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: pyridine; Dess-Martin periodane / dichloromethane / 1 h / 20 °C
2.1: triethyl borane; potassium tert-butylate / toluene; tetrahydrofuran / 0.17 h / 110 °C
2.2: Reflux
3.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
4.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
4.2: Reflux
5.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme
53573-82-3

3,17β-bis(2-tetrahydropyranyloxy)estra-1,3,5(10)-triene-6-one

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: triethyl borane; potassium tert-butylate / toluene; tetrahydrofuran / 0.17 h / 110 °C
1.2: Reflux
2.1: potassium tert-butylate / tetrahydrofuran; methanol / 70 °C
3.1: hydrogenchloride / dichloromethane; methanol; water / 1 h
3.2: Reflux
4.1: acetic acid; dihydrogen peroxide / water; ethyl acetate
View Scheme

C29H44O3

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
2: water; sodium hydroxide / methanol / 5 h / 20 °C
3: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
4: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
2: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
3: water; sodium hydroxide / methanol / 5 h / 20 °C
4: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

C31H44O4

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: water; sodium hydroxide / methanol / 5 h / 20 °C
2: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
2: water; sodium hydroxide / methanol / 5 h / 20 °C
3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

C27H40O2

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
2: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

C36H51F5O4S

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: water; sodium hydroxide / methanol / 5 h / 20 °C
2: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: acetic acid; dihydrogen peroxide / ethyl acetate / 0 - 25 °C
2: sodium hydroxide / methanol / 25 °C
View Scheme
148757-88-4

4,4,5,5,5-pentafluoro-1-pentanethiol

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
2: water; sodium hydroxide / methanol / 5 h / 20 °C
3: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
4999-76-2

3,17β-diacetoxy-estra-3,5-diene

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
1.2: 2 h / 0 °C / Reflux; Inert atmosphere
2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
2.2: 0.5 h / -20 - 20 °C
3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
4.1: water; sodium hydroxide / methanol / 5 h / 20 °C
5.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme
Multi-step reaction with 6 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide; water / 1.25 h / 0 - 7 °C / Inert atmosphere
1.2: 2 h / 0 °C / Reflux; Inert atmosphere
2.1: copper(I) bromide / tetrahydrofuran / 0.75 h / -20 °C / Inert atmosphere
2.2: 0.5 h / -20 - 20 °C
3.1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C
4.1: 2,2-dimethoxy-2-phenylacetophenone / chloroform / 5 h / 20 °C / Inert atmosphere; UV-irradiation
5.1: water; sodium hydroxide / methanol / 5 h / 20 °C
6.1: acetic acid; dihydrogen peroxide / ethyl acetate / 16 h / 20 °C
View Scheme

C11H10F5NO5S

129453-61-8

fulvestrant

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ethanol / 6 h / 65 °C
2: N,N-dimethyl-formamide / 20 °C
3: acetic acid; dihydrogen peroxide / ethyl acetate
View Scheme
129453-61-8

fulvestrant

109-94-4

formic acid ethyl ester

403656-82-6

ICI 182,780-17β-formate

Conditions
ConditionsYield
With toluene-4-sulfonic acid Heating;100%
98-88-4

benzoyl chloride

129453-61-8

fulvestrant

261506-25-6

ICI 182,780-3-benzoate

Conditions
ConditionsYield
With potassium hydroxide In dichloromethane at 0 - 20℃; for 2.5h; Schotten-Baumann reaction;99%
With potassium hydroxide In dichloromethane Esterification;
141-78-6

ethyl acetate

129453-61-8

fulvestrant

261506-24-5

ICI 182,780-17β-acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid for 6h; Heating;97%
129453-61-8

fulvestrant

229625-50-7

di-tert-butyl chloromethyl phosphate

di-tert-butyl ((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentyl sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)methyl phosphate

Conditions
ConditionsYield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.0833333h; Inert atmosphere;
Stage #2: di-tert-butyl chloromethyl phosphate In tetrahydrofuran at 70℃;		95.38%
129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-deca hydro-6H-cyclopenta[a]phenanthren-3-yl sulfurofluoridate

Conditions
ConditionsYield
With fluorosulfonyl fluoride; triethylamine In acetonitrile at 20℃; for 1h; chemoselective reaction;90%
With fluorosulfonyl fluoride; triethylamine In dichloromethane at 20℃; for 12h; Sealed tube;72%
103366-74-1

2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate

129453-61-8

fulvestrant

C84H131F5O21S

Conditions
ConditionsYield
Stage #1: fulvestrant With boron trifluoride diethyl etherate In 1,2-dichloro-ethane at -20℃;
Stage #2: 2,3,4,6-Tetra-O-pivaloyl-α-D-glucopyranosyl trichloroacetimidate In 1,2-dichloro-ethane Further stages.;		80%
129453-61-8

fulvestrant

ICI 182,780-17-ketone

Conditions
ConditionsYield
With oxalyl dichloride; dimethyl sulfoxide; diisopropylamine In 1,2-dichloro-ethane at -70 - 20℃; Swern oxidation;65%
990-91-0

dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate

129453-61-8

fulvestrant

dibenzyl ((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl) phosphate

Conditions
ConditionsYield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.0833333h;
Stage #2: dibenzyl [[bis(benzyloxy)phosphoryl]oxy]phosphonate In tetrahydrofuran at 70℃; for 18h;		62.99%
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

129453-61-8

fulvestrant

C52H75F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;58%
108-30-5

succinic acid anhydride

129453-61-8

fulvestrant

4-(((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)-4-oxobutanoic acid

Conditions
ConditionsYield
With dmap; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 16h;54.08%
5070-13-3

bis-(p-nitrophenyl) carbonate

13518-40-6

L-valine tert-butylester hydrochloride

129453-61-8

fulvestrant

(2S)-tert-butyl 2-(((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H cyclopenta[a]phenanthren-3-yloxy)carbonylamino)-3-methylbutanoate

Conditions
ConditionsYield
Stage #1: bis-(p-nitrophenyl) carbonate; L-valine tert-butylester hydrochloride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: fulvestrant With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;		48.8%
...Expand
1118-68-9

dimethylaminoacetic acid

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl dimethylglycinate

Conditions
ConditionsYield
Stage #1: dimethylaminoacetic acid; fulvestrant With dmap In dichloromethane at 0℃; for 0.166667h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;		46.77%
5070-13-3

bis-(p-nitrophenyl) carbonate

16874-17-2

L-phenylalanine tert-butyl ester

129453-61-8

fulvestrant

(2S)-tert-butyl 2-(((7R,8R,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-(4,4,5,5,5-pentafluoro pentylsulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yloxy)carbonylamino)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: bis-(p-nitrophenyl) carbonate; L-phenylalanine tert-butyl ester With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
Stage #2: fulvestrant With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; Inert atmosphere;		33.96%
...Expand
3235-69-6

morpholin-4-ylacetic acid

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-morpholinoacetate

Conditions
ConditionsYield
Stage #1: morpholin-4-ylacetic acid; fulvestrant With dmap In dichloromethane at 0℃; for 0.0833333h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 0℃; for 2h;		33.07%
39539-66-7

4-methyl-piperazine-1-carbonyl chloride

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 4-methylpiperazine-1-carboxylate

Conditions
ConditionsYield
Stage #1: fulvestrant With dmap; potassium carbonate In acetonitrile at 20℃; for 0.5h;
Stage #2: 4-methyl-piperazine-1-carbonyl chloride at 0 - 20℃; for 18h;		31.46%
112-37-8

undecylenic acid

129453-61-8

fulvestrant

C43H67F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;27.7%
4497-04-5

3-morpholin-4-ylpropionic acid

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 3-morpholinopropanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;26.37%
129453-61-8

fulvestrant

229625-50-7

di-tert-butyl chloromethyl phosphate

di-tert-butyl ((((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl- 7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl)oxy)methyl) phosphate

Conditions
ConditionsYield
Stage #1: fulvestrant With potassium tert-butylate In tetrahydrofuran at 70℃; for 0.25h;
Stage #2: di-tert-butyl chloromethyl phosphate In tetrahydrofuran at 70℃; for 7h;		26.14%
814-49-3

diethyl chlorophosphate

129453-61-8

fulvestrant

diethyl ((7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl) phosphate

Conditions
ConditionsYield
Stage #1: fulvestrant With tetrabutylammomium bromide; sodium hydroxide In chloroform; water at 20℃; for 0.5h;
Stage #2: diethyl chlorophosphate In chloroform; water at 20℃; for 16h;		24.5%
129453-61-8

fulvestrant

54699-92-2

(4-Methyl-piperazin-1-yl)-acetic acid

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-(4-methylpiperazin-1-yl)acetate

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 16h;24.37%
37386-15-5

2-(pyrrolidin-1-yl)acetic acid

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-(pyrrolidin-1-yl)acetate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;23.24%

5,7,7-trimethyl-2-(1,3,3-trimethylbutyl)-octanoic acid

129453-61-8

fulvestrant

C50H81F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;23.2%
57-10-3

1-hexadecylcarboxylic acid

129453-61-8

fulvestrant

C48H77F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;22%
15790-93-9, 15790-94-0, 4189-02-0

undec-2-enoic acid

129453-61-8

fulvestrant

C43H65F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;21.5%
129453-61-8

fulvestrant

docosahexa-4,7,10,13,16,19-enoic acid

C54H77F5O4S

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 48h;21.1%
129453-61-8

fulvestrant

69-72-7

salicylic acid

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 2-hydroxybenzoate

Conditions
ConditionsYield
Stage #1: fulvestrant; salicylic acid With dmap In dichloromethane at 0℃; for 0.0833333h;
Stage #2: With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 16h;		18.92%
6300-04-5

3-dimethylaminopropionic acid

129453-61-8

fulvestrant

(7R,8R,9S,13S,14S,17S)-17-hydroxy-13-methyl-7-(9-((4,4,5,5,5-pentafluoropentyl)sulfinyl)nonyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthren-3-yl 3-(dimethylamino)propanoate

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 12h;18.62%
Raw Materials
153004-31-0
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Chemistry

Structure of Fulvestrant (CAS NO.129453-61-8):

IUPAC Name: (7R,8R,9S,13S,14S,17S)-13-Methyl-7-[9-(4,4,5,5,5-pentafluoropentylsulfinyl)nonyl]-7,8,9,11,12,14,15,16,
17-decahydrocyclopenta[a]phenanthrene-3,17-diol
Molecular Formula: C32H47F5O3S
Molar Mass: 606.77  g/mol
Flash Point: 361.9 °C
Boiling Point: 674.8°C at 760 mmHg
Vapour Pressure: 3.95E-19  mmHg at 25 °C
Density: 1.201 g/cm3
Storage Temp.: 2-8 °C 
Index of Refraction: 1.521
Molar Refractivity: 154.04 cm3
Molar Volume: 505.1 cm3
Surface Tension: 41.9 dyne/cm 
XLogP3: 9.2
H-Bond Donor: 2
H-Bond Acceptor: 8
Rotatable Bond Count: 14
Tautomer Count: 9
Exact Mass: 606.316607
MonoIsotopic Mass: 606.316607
Topological Polar Surface Area: 57.5
Heavy Atom Count: 41 
Canonical SMILES: CC12CCC3C(C1CCC2O)C(CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)[C@@H](CC4=C3C=CC(=C4)O)CCCCCCCCCS(=O)CCCC(C(F)(F)F)(F)F
InChI: InChI=1S/C32H47F5O3S/c1-30-17-15-26-25-12-11-24(38)21-23(25)20-22(29(26)27(30)13-14-28(30)39)10-7-5-3-2-4-6-8-18-41(40)19-9-16-31(33,34)32(35,36)37/h11-12,21-22,26-29,38-39H,2-10,13-20H2,1H3/t22-,26-27+,28+,29-,30+,41/m1/s1
InChIKey: VWUXBMIQPBEWFH-WCCTWKNTSA-N
Product Categories: Intermediates & Fine Chemicals; Pharmaceuticals; Nuclear Receptors

Uses

 Fulvestrant (CAS NO.129453-61-8) is indicated for the treatment of hormone receptor positive metastatic breast cancer in postmenopausal women with disease progression following anti-estrogen therapy.

Safety Profile

RTECS: KG7623000

Specification

 Fulvestrant (CAS NO.129453-61-8) is also named as 7alpha-(9-((4,4,5,5,5-Pentafluoropentyl)sulfinyl)nonyl)estra-1,3,5(10)-triene-3,17beta-diol ; CCRIS 8741 ; Faslodex ; HSDB 7658 ; ICI 182,780 ; ICI 182780 ; UNII-22X328QOC4 ; ZM 182780 . Fulvestrant (CAS NO.129453-61-8) is white powder.