• Name

  Estra-1,3,5(10)-triene-3,17-diol,7-[9-[(4,4,5,5,5-pentafluoropentyl)thio]nonyl]-,17-acetate,(7a,17b)-

• EINECS 1592732-453-0
• CAS No. 875573-69-6
• Article Data4
• CAS DataBase
• Density 1.19 g/cm³
• Solubility
• Melting Point
• Formula C₃₄H₄₉F₅O₃S
• Boiling Point 631.4±55.0 °C(Predicted)
• Molecular Weight 632.819
• Flash Point
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms (7α,17β)-7-[9-(4,4,5,5,5-pentafluoropentyl)thio]nonyl]estra-1,3,5(10)- triene-3-diol-17oxyethyl;
• PSA 71.83000
• LogP 10.23790

Synthetic route

875573-66-3

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

C6H9F5N2S*ClH

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Stage #1: (+)-(7α)-[9-bromononyl]estra-1,3,5(10)-triene-3-ol-17β-yl acetate; C6H9F5N2S*ClH With potassium hydroxide In N,N-dimethyl-formamide at 0 - 10℃; for 1.5h; Stage #2: With acetic acid In ethyl acetate; N,N-dimethyl-formamide for 0.166667h;	85%

252947-01-6

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

C29H44O3S

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 48h; Inert atmosphere; Reflux;	80%

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

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide; water at 20℃; for 0.6h; Product distribution / selectivity;

252947-01-6

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

BrH*C29H46N2O3S

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
With sodium hydroxide In N,N-dimethyl acetamide; water at 20℃; for 1h; Product distribution / selectivity;

C29H44O3

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: copper(I) bromide; lithium bromide / acetonitrile / 24 h / 20 °C 2: 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Reflux 3: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 4: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

C31H44O4

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 2,2'-azobis(isobutyronitrile) / toluene / 1.5 h / Reflux 2: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 3: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

C33H48O5S

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 2: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

434-22-0

19-nortestosterone

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions

Yield

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'-azobis(isobutyronitrile) / toluene / 1.5 h / Reflux 6.1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 7.1: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

148043-73-6

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

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 4 h / 20 °C / Inert atmosphere 2: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 2 h / 20 °C / Cooling with ice 2: ethanol / Reflux 3: sodium hydroxide / water; methanol / 24 h / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 3 steps 1.1: thionyl chloride; triethylamine / dichloromethane / 2 h / 0 - 20 °C 2.1: isopropyl alcohol / 80 - 85 °C 3.1: potassium hydroxide / N,N-dimethyl-formamide / 1.5 h / 0 - 10 °C 3.2: 0.17 h View Scheme

4999-76-2

3,17β-diacetoxy-estra-3,5-diene

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions

Yield

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'-azobis(isobutyronitrile) / toluene / 1.5 h / Reflux 5.1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 6.1: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

2590-41-2

6-dehydro-19-nortestosterone acetate

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions

Yield

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'-azobis(isobutyronitrile) / toluene / 1.5 h / Reflux 4.1: hydrazine hydrate / tetrahydrofuran / 4 h / 20 °C 5.1: potassium carbonate / acetonitrile / 48 h / Inert atmosphere; Reflux View Scheme

(7α,17β)-7-[9-(methanesulfonyloxy)nonyl]estra-1,3,5(10)-triene-3,17-diol-17-acetate

S-(4,4,5,5,5-pentafluoropentyl)isothiourea methanesulfonate

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
With sodium hydroxide In methanol; water for 24h; Inert atmosphere; Reflux;

252947-01-6

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

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol / Reflux 2: sodium hydroxide / water; methanol / 24 h / Inert atmosphere; Reflux View Scheme

1,1,1,2,2-pentafluoro-5-chloro-n-pentane

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: isopropyl alcohol / 80 - 85 °C 2.1: potassium hydroxide / N,N-dimethyl-formamide / 1.5 h / 0 - 10 °C 2.2: 0.17 h View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

153004-31-0

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

Conditions

Conditions	Yield
Stage #1: 17-O-acetyl-S-deoxo-fulvestrant With potassium hydroxide In methanol at 40℃; for 2h; Stage #2: With acetic acid In methanol; ethyl acetate for 0.166667h;	78.2%
With methanol; potassium hydroxide at 20℃; for 1 - 4h; Product distribution / selectivity;

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

261506-24-5

ICI 182,780-17β-acetate

Conditions

Conditions	Yield
With sodium periodate In tetrahydrofuran; methanol; water at 5 - 20℃;

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

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

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / -10 °C 2: potassium acetate; tricyclohexylphosphine; palladium diacetate / acetonitrile / 80 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: pyridine / dichloromethane-d2 / -10 °C 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C View Scheme
Multi-step reaction with 2 steps 1: pyridine / dichloromethane 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / dichloromethane / -10 °C 2: potassium acetate; tricyclohexylphosphine; palladium diacetate / acetonitrile / 80 °C / Inert atmosphere 3: potassium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 20 °C View Scheme
Multi-step reaction with 3 steps 1: pyridine / dichloromethane-d2 / -10 °C 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C 3: potassium hydroxide; methanol / tetrahydrofuran / 4 h / 0 - 20 °C View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

C38H58BF5O4S

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / dichloromethane / -10 °C 2: potassium acetate; tricyclohexylphosphine; palladium diacetate / acetonitrile / 80 °C / Inert atmosphere 3: potassium hydroxide / methanol; tetrahydrofuran / 4 h / 0 - 20 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

358-23-6

trifluoromethylsulfonic anhydride

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

Conditions

Conditions	Yield
With pyridine In dichloromethane at -10℃;	0.7 g
With pyridine In dichloromethane-d2 at -10℃;
With pyridine In dichloromethane

875573-69-6

17-O-acetyl-S-deoxo-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)boronic acid

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: pyridine / dichloromethane-d2 / -10 °C 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C 3: potassium hydroxide; methanol / tetrahydrofuran / 4 h / 0 - 20 °C 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C View Scheme
Multi-step reaction with 4 steps 1: pyridine / dichloromethane 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C 3: methanol; potassium hydroxide / tetrahydrofuran 4: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 °C View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

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

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / dichloromethane 2: palladium diacetate; tricyclohexylphosphine / acetonitrile / 80 °C 3: methanol; potassium hydroxide / tetrahydrofuran View Scheme

875573-69-6

17-O-acetyl-S-deoxo-fulvestrant

129453-61-8

fulvestrant

Conditions

Conditions	Yield
With sodium periodate In methanol; water at 20℃; for 24h; Cooling with ice;

(7a,17b)-7-[9-[(4,4,5,5,5-Pentafluoropentyl)thio]nonyl]-estra-1,3,5(10)-triene-3,17-diol 17-acetate Chemical Properties

(7a,17b)-7-[9-[(4,4,5,5,5-Pentafluoropentyl)thio]nonyl]-estra-1,3,5(10)-triene-3,17-diol 17-acetate Specification